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Apr
9
6
min

The Legal Playbook for Scrappy Startups

Creating your first legal documents doesn’t have to be expensive or hard. Here’s what I’ve seen real startups do to get off the ground with their legal documents!

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Creating your first legal documents doesn’t have to be expensive or hard.

When you are signing your first customer, you probably don’t have time or money for fancy legal docs.

Speed, simplicity, and survival are the goals.

If you have funding or lots of customers, yes, by all means, get a good, startup-friendly lawyer.

But on day 1? You’re just trying to see if customers will pay you to solve this problem!

Here’s what I’ve seen real startups do to get off the ground with their legal documents!


Disclaimer: I’m not a lawyer blah blah blah. If for some reason you take this as legal advice, that is a terrible idea by you and you are reading the wrong blog. I’m just a startup operator trying to help founders be scrappy!


Your First Terms of Service & Privacy Policy

  1. Find a large company with a similar business model.

  2. Use their Terms of Service and Privacy Policy as a blueprint.

  3. Update with your company name, location, pricing, etc.

  4. Skim to make sure everything sounds reasonable.

We used Salesforce’s Terms of Service as our blueprint at Pardot for hundreds of customers and several years — until we were actually acquired by Salesforce!

Surprise bonus: it was easy to switch customers over to the new Terms of Service 😉


Your First Contract

  1. Add your logo (or company name in a professional font) to a Google Doc

  2. Add a table with a package and/or line items (e.g. what’s included)

  3. Summarize pricing and contract term at the bottom

  4. Reference your Terms of Service as a link

  5. Save as PDF

  6. BONUS: Send via DocuSign or other e-sign tool for easy signature.

We used proposals and contracts made in Google Docs for 5+ years at Pardot and Rigor.


Your First Investment

  1. Use a YCombinator SAFE. (Simple Agreement for Future Equity)

  2. All YCombinator founders and many others use these. Like the name says, it’s a simple investment vehicle for your first investors — angels, family and friends, pre-seed VCs.

  3. No need to reinvent the wheel. Focus on growing your business instead!


Your First Patents, Trademarks, and IP

Okay, legit disclaimer here: I know B2B SaaS. Where trademarks, IP, and patents are not a factor in the early days.

Everything about your business, product, and messaging is changing constantly. You’re figuring things out and spending time with customers — not on legal filings!

Eventually, yes, when you’re “big” (however you define this), you’ll want to have some legal protections in place for your brand and technology.

I think it’s different in other areas — biotech, deep tech, higher ed scientific research, inventing rockets and shit. But I’ve never built a rocket or invented a cancer drug so I can’t speak to that.

In software, it’s likely that other people will be building in the space too. They will see what you’re building and if it’s good, they’ll copy it. Or they’ll already have the same idea because it’s a big market with a lot of demand to solve the problem.

You can’t worry if a competitor copies something. One feature or pricing package or marketing campaign is not your competitive advantage. It’s ALLLL the things you’re doing as a business that make your boat rise — how you sell, who you target, what you prioritize, culture and talent.

If you’re in the right market, there will be multiple winners! And once you have the initial market, it’s all about execution.


Founder Agreements

  1. Clarify what % ownership everyone has up front in writing.

  2. Include vesting — e.g. must be at the company at least 1 year and vests over 4 years.

  3. You don’t need to get a lawyer involved but be clear and no 50/50 splits!

  4. Every business needs a clear “tie-breaker” and CEO (aka 51/49 split).

Don’t kick the can on this! If you can’t talk about it with your co-founder, you’re not ready to start a business together. (True for marriage and finances too! I digress…)

If you wait, the discussion is 10x harder and previous conversations are more likely to be misremembered or misinterpreted.


Employee Agreements

  1. Find a template online.

  2. Or not. You can also have employees sign agreements later. I’ve signed updated employee paperwork well after a start date.

  3. If you have 2 contractors or 2 friends working for free, wait until you have some traction before spending time on this!

  4. Stock option agreements included here too. (Great primer from Fred Wilson)

These agreements include things that are important but don’t come up that often: the code you write belongs to the company, you can’t leave and start a competitor, no selling state secrets or we have to kill you, etc.

If you have 100s of employees, you definitely want these!

If you are still small and mighty, you’re better off spending time getting customers.


Other Business Docs

Go Cooley is a legal template tool that was recommended to me by a lawyer friend (BUT DOES NOT CONSTITUTE LEGAL ADVICE! ← I’m supposed to add that disclaimer 😁).

Other founders are also a good source of templates. Most folks are happy to share their policies or legal docs as a baseline.

If you’re part of an accelerator or other startup group, they’ll probably have some boilerplate docs.

AI is changing things quickly and legal AI is a great use case. For now, it also hallucinates which is why I’d still check anything against a similar, real world document produced by a corporate lawyer whenever you can!

Any other favorite tools? I’d love to hear!


High Class Problems

Here’s your friendly reminder that legal issues people (especially lawyers 😉) warn you about…fall into the “good problems to have” bucket!

Most importantly, people who are busy winning don’t have time to launch legal battles. Even if they can afford it, it’s not worth the energy or distraction!


Lawyers Are Awesome

I want to be very, very clear.

If your company is growing and doing well, you should have a lawyer. I’ve worked with many awesome lawyers who have been tremendously helpful.

All the things I said to hack together? Once you get traction, you want a lawyer to review those hacky docs!

Doing enterprise contracts regularly? You’ll definitely need a lawyer on retainer.

If you have investors, they will probably want you to have your legal ducks (mostly) in a row. The larger the fundraise, the tighter legal needs to be.

But when you’re getting started?? Don’t make “I need a lawyer before I can XYZ…” a hurdle!

The best way to get started is to get started. Find that authentic demand!


Any favorite resources, templates, or legal AI resources to share? What’s your best money or time saving legal tip??

April 9, 2024
Apr
2
2
min

Good At Sales But Bad At Customer Success? Here's How To Fix That

Great sales people make great founders. And great sales people make terrible customer success managers. Okay, okay! I’m kidding. For myself, the opposite was true. Mediocre at sales, excellent at customer success 😁 There are many similarities between great sales and great customer success:

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Great sales people make great founders.

And great sales people make terrible customer success managers.

Okay, okay! I’m kidding.

For myself, the opposite was true. Mediocre at sales, excellent at customer success 😁

There are many similarities between great sales and great customer success:

  • Cares about customers, relationship-oriented

  • Asks great questions, listens carefully

  • Understands motivation, customizes approach

  • Hard-working, responsive, well-prepared, generous

That said, I’ve talked to several founders who are great at sales who have struggled with post-sale customer interactions and feedback.

Why?

Founders get hammered left and right by naysayers.

You can’t sell it.
It won’t work.
We don’t want it.
No. No. No.

In an investor meeting, you have to be ready to knock down every objection.

In a sales meeting — especially in the early days — you are knocking down objections too. Objections like your lack of funding, product maturity, app security, and well-funded competition.

Then you go home and have to explain to your mom why starting a company is better than law school.

You don’t mind. You like selling, being a rebel, and proving people wrong.

Then you have a customer call.

They tell you what’s not working.

It’s okay though.

You are ready to handle their objections, prove them wrong, explain why your idea is the best!

Except that’s not the right thing anymore.

When a customer says something sucks, you have to say, “Tell me more.

A customer says your product is wrong, you say, “Help me understand.

A customer is mad, you say, “I’m sorry. We messed up.

The quickest way to shut down customer feedback is to argue, defend, or challenge.

You want them to tell you the bad stuff.

But it’s a totally different mindset than every other area of the business!

So when you get on a customer call, remember:

  • They’re on your side

  • Humility over bravado

  • You’ll get more if you agree

  • Feedback is a gift (love this from CBQ!)

  • Open questions not challenging ones

  • This isn’t one of those jerk-faced investors! 😉

Yes, if a customer is at-risk of churning, being unreasonable, or likes debating, then by all means activate the objection-busting!

But if it’s a normal customer interaction where you want to maximize learning, engagement, and feedback, then put your very successful sales mindset away and wear that cuddly, feel-good customer success hat!


What tips do you have for switching between sales and customer success? Do you notice a difference in strategies with each? What mindset comes more naturally to you?

April 2, 2024
Mar
26
7
min

The Only Framework You Need to Delegate Like a Pro

We recently talked about the importance of clarifying decision-making and delegation at a startup — especially if someone is going to be out on leave. Which reminded me… Effective delegation and clarity around decision making is IMPORTANT ALL THE TIME!!

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We recently talked about the importance of clarifying decision-making and delegation at a startup — especially if someone is going to be out on leave.

Which reminded me…

Effective delegation and clarity around decision making is IMPORTANT ALL THE TIME!!

When Pardot was acquired by Exact Target (prior to Exact Target being acquired by Salesforce 9 months later - ha!), we went through an amazing manager training.

Exact Target was a high growth tech company with 2000+ employees so talent development was key.

They had an amazing in-house training curriculum based on Fierce, Inc.

I still have my 8 card cheat sheet from the training 10+ years ago!!

I ruthlessly purge clutter so this speaks volumes to the quality of this tiny notebook.

I especially loved their decision-making framework.

Don’t have time to fly to Indy and spend 3 days in a conference room to do the training in-person? I got you.

Here’s your ultimate guide to startup delegation!


Decision Tree Framework

🍃 1. Leaf Decision

  • Make the decision.

  • Act on it.

  • Do not report the action you took.

“Just do it. No need to tell me.”

🌿 2. Branch Decision

  • Make the decision.

  • Act on it.

  • Report the action you took daily, weekly, or monthly.

“Do it but keep me in the loop.”

🎋 3. Trunk Decision

  • Make the decision.

  • Report your decision before you take action.

“Run it by me before you do it.”

🌳 4. Root Decision

  • These decisions are made with input from many people.

  • Or, these decisions I’m not willing to delegate.

“I need to be the one handling this.”


How Do I Use This Framework?

1. Company-wide

Explain the framework to everyone on the team.

Then it becomes a shared company language for decision making:

Is this a leaf or a branch?
I know that’s a branch but want to try it as a trunk?
Which of these tasks are leaves, branches, trunks, roots?

2. Personal clarity

Use this framework to self-assess.

What instructions do you give your team?

Are you clear where they have autonomy? Do you honor that autonomy or second guess them?

When and where do you need to be looped in?

Are you too in the weeds or not close enough to key decisions?


How Do I Decide What To Delegate?

Wondering what you should delegate? Here are the questions we asked in our Fierce training. We matched up with a peer to “real play” and having someone ask and discuss was so helpful!

What activity or responsibility is no longer the best use of my time?

Make a list. Get someone to ask you this question and discuss it. Ask your team or a loved one. They may see things you don’t! Do a company-wide brainstorming sesh where everyone asks this question of themselves.

To whom would I like to give this responsibility?

Could be a person. But could also be a technology or maybe it can be dropped all together!

At what level?

Time for our decision tree! Is this a leaf, branch, trunk?


Who Do I Delegate To?

Um? Anyone?

Even if you’re a team of 1, you can hire a virtual assistant, enlist a neighborhood kid to handwrite thank you cards, or do a task/skill swap with another professional.

Hire an intern.

Let your junior teammate take more on.

Ask that high paid consultant to step it up.

You’ll be pleasantly surprised that people want to help and are often excited for a new challenge.


But, I Can’t Because…

Oh, hello, excuses! Nice to see you.

Get ready for me to punch you in the face.

No one else will want to do this. This is grunt work.

FACE PUNCH 👊 → What feels boring or menial to you, may be interesting and educational to someone else. They may be excited to improve on the process or it may align with their skills or personality. Don’t assume you know what others want.

No one can do it as well as I can. They are going to make mistakes.

FACE PUNCH 👊 → You make mistakes too. You just forgive yourself a lot quicker than you forgive others for the same mistakes. (Speaking from experience here…)

It’s reasonable to expect a learning curve. THAT’S WHY THERE IS A TRUNK DECISION. Start by having the delegatee (d-alligator? 🐊) run it by you, when they get pretty good, turn that decision into a branch. Don’t go from root to leaf!

No task is too small for me. I roll up my sleeves with the team.

FACE PUNCH 👊 → I see executives who are bogged down doing admin tasks to “prove” they still can or to take the burden off their team.

While well intentioned, there is a significant downside.

They are burned out, not doing the high value tasks only a CEO can do, depriving their team of growth opportunities, or all of the above!

Yes, there’s servant leadership blah blah blah. If your CEO is doing dumb shit instead of high value stuff, as an employee, you will be annoyed. Especially if the company is not moving forward.

This is DIFFERENT than a leader who is intentionally carving out time to walk the factory floor, meet with employees, or handle a customer support ticket to stay close to the front lines. That’s cool. O’Daily approved.

But shopping for the team snacks when an intern could or nitpicking grammar in a marketing blog? Denied!

We can’t afford it.

FACE PUNCH 👊 → How many hours would it free up? What could you do with those hours? If you can use it to bring in more revenue, there’s clear ROI on spending some money to delegate.

There are also very low cost options — offshore resources, college students, bartering, and more. You’ll be surprised at how creative you can get once you open the delegation door!

But I like doing that thing I know I should delegate.

FACE PUNCH 👊 → First, there’s probably 10 other things you don’t like doing, so start by delegating those.

Then, take a hard look at yourself to ask, why won’t I give my Legos away?

Am I afraid of sucking?

Do I want to scale with my company?

What got you here won’t get you there. Delegating is part of getting to the next level!

Or, if you genuinely love the work that you know you should delegate, find someone for that other role you don’t want to do.

Not every founder wants to be CEO and that’s okay!


What If I Don’t Have Someone To Delegate To?

Real talk.

Sometimes you really don’t have someone to delegate to.

Team is small, money is tight.

MAYBE a $10/hr offshore virtual assistant can be helpful. MAYBE you can find a free intern who just wants the experience.

But maybe not.

Here’s another delegation question to ask:

What can I automate?

Helloooooo, ChatGPT. Have you heard of it? 😂

It was amazing to work with Mark Isham at Rigor. He was a founder who could code anything. He built so many amazing internal tools because if he had to do a task manually more than once, he turned it into code! Not all of us can do that BUT we can do more of it than we think.

What can I subtract or pause?

What are you doing that can be paused or is no longer a priority?

Subtracting could mean — send shorter emails, ignore messages on LinkedIn, or deleting Tiktok.

Or it could mean letting go of the not-good-fit-customer, cutting the buggy feature that no one uses, or doing fewer general marketing events to focus on the highly targeted ones.

Personally, every time I audit my time, priorities, and calendar, I find something that’s outdated, no longer important, or could be - GASP - delegated. 😉

It’s a great feeling to find extra time in the schedule, and to remember how awesome, capable, and helpful teammates, tools, and services are!


What are you going to start delegating after reading this post?? What delegation frameworks or tools have you used at your company? Any other tips?

March 26, 2024
Mar
19
5
min

Want To Be the Best? First, You Need to Be the Worst

To take on a new challenge, you have to accept the single most important truth: at first, you will suck.

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It’s the most important part of taking on a new challenge.

A challenge like:

  • Building a company

  • Running a marathon

  • Writing a newsletter

No, it’s not all that lame stuff like set a goal, spend 30 minutes per day, find a mentor, blah blah blah.

Okay, fine. That’s excellent, research-based advice.

But before you can even get to the point where that matters, you have to accept one truth that will unlock all future growth and achievement:

You are going to suck.

At first.

When you’re a high achiever, how do you tap into the growth mindset and do new things (especially publicly) where you may not be good?

Plan to suck!

I like to know that I am going to be really bad at something at first.

I expect it.

Which makes it easier to get started!

And once you get started, you start learning. And getting better.

Of course, getting better, often looks like doing badly. But that’s okay! You planned for that.

You know the first few attempts will be WAY harder and you’ll do WAY worse because you planned for that!

It doesn’t derail you. It lets you know the process is working and it will get easier.

The more you plan to suck, the sooner you can get started, the sooner the suck will be over!

One day, in the not so distant future, you realize:

Wow! I’m no longer terrible!
What used to take me 10 days of agony, I can do in 30 minutes.
My armpits aren’t (that) sweaty.
I’m getting pretty good feedback.
I could layer on another goal!


How This Applies To Startups

The idea that you will suck to start (and you should plan around that) is exactly why we recommend:

So much of startups is starting (duh! it’s in the name!) and learning.

Taking action, figuring it out as you go, discarding incorrect assumptions, and being faster than your competitors.

If you’re willing to be embarrassingly bad to start, you will learn more and faster!


What About Preparation?

You may ask: If you know you’re going to suck, why don’t you just prepare better?

First of all, I do!!!! I’m an over-preparer.

But here’s why that doesn’t work:

You don’t know what you’re going to suck at!!!!!!!!

Or to use my least favorite phrase in business (that you will hear 1000 times if your company is being acquired):

You don’t know what you don’t know🧑‍💼🤓🧑‍💼🤓

Or to put it a more positive, less annoying way:

It takes a while to find your strengths and what works for you.

Preparation can help. I recommend preparing (especially for Q&A!). But everyone has a plan until they get punched in the face. Or, um, hear real customer feedback, get on stage, or see the faces of investors when they’re sharing their pitch.

So prepare…then get it into the real world asap so the improvement can begin!


Real Life Examples of Being The Worst & Getting Better

#1 Fireside Chat

In my first fireside chat, I was afraid I’d forget the questions.

So I memorized the questions and asked them exactly. Verbatim. No lead in.

As you can imagine, it was rather stiff and formal. 🤖

The next fireside chat I hosted, I was more conversational and fun. It was 10x better (and I didn’t forget any questions)!

#2 This Newsletter!

I took 3 months to start this newsletter.

Researching the best platform, trying to discover my voice, figuring out my brand.

(Sound familiar to any founders who would rather build than sell??? 😁😉)

Once I finally got started, my first posts took FOREVER to write. Like 8 hours for 500 words.

And they weren’t even good!

Over time, I learned:

  • the right amount of jokes (A LOT)

  • my writing works best with numbers, bullets, lists, line breaks, for easy skimming

  • if a post gets too long — make it 2 posts

  • how to add a photo to the thumbnail

  • what a good title looks like (aka get help from people better than me!)

#3 Many More Things

Here are some other things where I’ve been the worst before getting better:

  • First “inspirational” speech (spoiler alert: it was not inspiring…)

  • First Instagram video

  • First panel where I explained (poorly) what we did at Atlanta Ventures

  • First meetings with founders


2 Main Principles of “Planning To Suck”

1. It gets easier.

The first meeting, presentation, call, post, whatever — will take forever to prepare for! And it will be the worst! The second one will take less time but be better! Expect to invest the most time up front and for each effort to get incrementally better.

2. 3 months or 3 attempts.

I like to plan for 3 months or 3 attempts (depending on the type and frequency of the skill/project) of terribleness before I start to “figure something out.”

If I get to one of these milestones and I am still terrible, I do some soul searching.

Do I care enough to keep going? Have I given it a fair effort? Is there a belief or life constraint holding me back?


Share This With Your Team Too!

Adam Blitzer, the COO and co-founder of Pardot, beloved by Pardashians everywhere, used to say:

We’re going to make a lot of mistakes and that’s okay. We’re just going to keep learning.

It was the kindest, most empowering thing to say to young, high performers who had no idea what they were doing but cared a lot and worked hard!

It also created a bias towards action which increased the rate of learning exponentially.

Adam did a great job of talking about his learnings and mistakes publicly to let people know it really was okay:

I had us switch to a new tool and it didn’t work at all. I should have pulled the plug sooner.

My first sales meeting was terrible. I told them not to buy our product!

If you want to support your team and grow quickly, encourage people to try new things and be okay with the mistakes!


What challenge are you tackling? How do you get started on something new? What advice do you have on doing new things or helping your team do new things?

March 19, 2024
Mar
12
6
min

How VCs Are Approaching Valuations in 2024

“Show founders the VC math.” Learn 6 steps to valuations in 2024!

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I recently chatted Lisa Calhoun of Valor Ventures and asked her how their firm was handling the significant reset of company valuations between 2021 and now.

She had a great response that I think is helpful to everyone in Startupland, especially founders who are raising right now.

She said, “Show founders the VC math.”


Here’s what she meant — in 2 formats — since some founders only have 2 minutes and others love the deets!


TL;DR

Investors are looking for a 10x return based on current exits in your market.

Work backwards to figure out a current valuation with those market comps.


If that was gibberish to you, no problem! Here is the full explanation with math, valuation charts, action item, and OF COURSE, the O’Daily calling card, a numbered list!


1. Pursue a 10x return.

It’s venture capital industry standard to invest in companies that have the potential to 10x your initial investment.

If it’s an early stage — like seed or pre-seed — they’re likely looking for 10-20x since it’s higher risk.

Why?

Because VCs have bosses!

Their bosses are entities like hospitals, endowments, and pension funds, who are counting on the money invested to increase in value for their constituents.

So how do you get a 10x return?

You invest $1M into a startup in the hopes that in 5-10 years, your investment is worth $10M.

Why 10x?

  • Many companies will end up at 1x or 0x.

  • A few companies will be 3-5x.

  • If things go well, 1 or 2 companies will be big and “return the whole fund.”

So you need to have a path to 10x in every investment to cover the ones that inevitably won’t work out.

If you start out with an upper limit of only 5x, you’re screwed!

If you’re pre-Series A, it’s even riskier so you need to shoot for 20x potential returns.

ICYMI — same math applies for founders which is why I talk about picking a big market here, here, here, here, and here!!!


2. Study exits in your industry.

What companies in your industry recently had exits?

Usually this means being acquired, sometimes it’s going public.

What were the economics of those exits?

In other words, how much was the company worth compared to its revenue (or EBITDA for later stages)? 5x revenue? 10x revenue? 3x revenue?

Here is a chart of 2023 SaaS trends for reference and another great chart that showcases the range and factors of valuations across industries. Business model, sector, growth rate, recurring vs non-recurring revenue, future potential, and a myriad of other things can impact valuations.

Helpful to note: public market valuations directly impact early stage private companies. They set the benchmark and everyone starts doing math based on those “end game” numbers.

So what does this mean for your company right now?

Here’s a simple example:

  • Based on the 2023 SaaS trends data, if you have a B2B SaaS company in adtech, when (not “if”!) you get to $10M ARR, you’ll get a 7x multiple or $70M valuation.


3. Work backwards to today.

What is a reasonable best-case-scenario for your company?

What is the right valuation now that enables an investor to get a 10x return?

This means that for your hypothetical $70M exit, an investor would need to invest today at a $7M valuation.

I’ve built out an elaborate formula for this:

  • $7M * 10x = $70M

You’re welcome. 🧠🥳💰

Of course, this assumes that you can get to $10M ARR without more investment.

If you take more investment, there’s more dilution, so the valuation would need to be even lower today to get a 10x return later.

More math:

  • $7M * 10x = $70M You raise another round and everyone is diluted 20%…

  • The company has to do 20% better in the exit -OR- starting valuation is 20% less

  • $7M * 80% (aka 20% less) = $5.6M

  • So $5.6M for your current valuation with one round of dilution to get 10x return

Let’s add a second round of dilution just in case things don’t go exactly as planned:

  • $5.6M * 80% = $4.5M

  • Not surprisingly, if you’re around $1M in revenue, this $4.5M valuation is pretty close to the 4.8x multiple from this chart:

It’s obviously not an exact science but this is back-of-the-napkin math to show you how investors are thinking about valuations right now.

Want to do your own math?

Here’s a simple dilution calculator from Atlanta Ventures to map out more investment rounds, include an employee option pool, or test different scenarios!


4. Remember your fundraise amount signals valuation.

If you’re relatively new to the world of VC, here’s a reminder about the most important unspoken math:

  • VCs assume that you’re offering 15-25% of your company

  • Whatever your fundraise ask is ~20% of your company’s value

  • Put another way: Fundraise $$ Ask * 5 = Your Implied Valuation

Yes, there are exceptions and negotiations but this is a helpful ballpark.

When you ask for a high dollar, it implies a high valuation, not high dilution (e.g. willingness to offer 50% of your company).


5. Compare this valuation to yours.

The reckoning!

Take the VC math and compare it to your current fundraise and/or last round valuation.

Close? Far? Way far?

The market has changed drastically so 99% of companies that raised in 2021 or 2020 will not love the math they see.

This isn’t a reflection of you or your company!

You may have executed perfectly, crushed your forecast, got amazing customer feedback, built the best product, and still not see a number you like.

Everyone in Startupland understands the shift.

Even top founders (and investors!) can’t control things like timing, luck, and the stock market.


6. Decide what (if any) actions to take.

I share all this to provide info and awareness.

This is the math investors are doing.

You chose what action, if any, to take.

Oh, and by the way — there are still companies raising money on better-than-industry valuations.

I know 2 companies in Atlanta this year that raised money on a 2-3x valuation of their previous round.

So there may be no action to take!

Maybe you double down on your current strategy. Maybe you tweak expectations. Maybe this is a wakeup call for a big change.

There are many paths, all with tradeoffs. Such is the nature of startups!

As you think it through, here are some questions that may help.

Valuation & Action Plan Questions

  • If I raise a round at a “VC math” valuation, what does that look like for me and the team? What will the cap table look like afterward?

  • What kind of exit makes it “worth it” at a new valuation? How many years or dollars until we get there?

  • Can I make a compelling case for better-than-industry potential and returns?

  • How much money do we need to get to the next milestone (raise, breakeven point, traction)? Can we get there with less money? What does that look like?

  • Are there any investors that passed because of valuation? Do different economics change the conversation?

  • What have my current investors advised? (While I think it’s commendable to protect the interests of current investors, they should understand the market. They can put in money themselves if they are pushing for a certain valuation.)


What other tips do you have around fundraising or valuation with the market shifts?

Any terms or concepts in this post that I should explain further? There is a lot of industry jargon!

March 12, 2024
Mar
5
7
min

Having A Baby? 4 Startup-Friendly Steps To Prep For Your Leave 👶

Babies are like startups. They never go as planned, more expensive than you thought, and you can't not love them!!!! Here are my 4 recommendations (PLUS **TWO** TEMPLATES) to prep for parental leave at a startup!

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Yay babies!!!!!!

Very similar to startups.

They never go exactly as planned, more expensive than you thought, but you can’t not love them!!!!

Last week, we talked about free and low cost ways that startups can support expecting parents (even on a tight budget)!

This week is for the expecting parents!

Having done 2 parental leaves, at 2 different startups, both times as the first parent and/or mom to go out on leave, I’ve learned a few tricks along the way.

YES: high level structure, planning, communication
NO: Trying to cover every detail or scenario ahead of time

As we know, things at startups change quickly. By the time you update documentation, it’s out of date.

So, while it’s important to have some documentation, it’s a fool’s errand (aka exhausting and unnecessary) to overplan or cover every contingency.

Here are my 4 recommendations (PLUS **TWO** TEMPLATES) to prep for parental leave!


1. Set up a password management tool.

The most high tech recommendation on this list.

Get yerself a password tool so you can easily share logins, store credit card info, and whatever else you don’t even realize you use regularly.

Benefits:

  • Security, duh. Spreadsheets of passwords are a normal but terrible startup practice. Password managers let you share passwords securely. Not that Slack or a Google Doc isn’t a good option. 🙃🥴😂

  • Control access to the sharing of passwords or other sensitive info — including keeping track of who has access to what (aka that intern from 3 years ago who can still login to your AWS account…).

  • Database — it’s easy to miss or forget a tool if you make a list. A password manager gives you a comprehensive list on-demand, no remembering necessary.

  • Always up-to-date. No need to update a separate doc or reshare a new pw with someone. If you update a password, it pushes updates automagically to anyone else sharing that login.

I like LastPass (I’ve used it for a long time and it does what I need) but there are other good ones too.


2. Create a point-of-contact spreadsheet.

Less is more when it comes to product design and parental leave documents.

Here is my favorite format for a parental leave planning document:

It’s a single-source-of-truth spreadsheet to be circulated across the company, pinned in a Slack channel, reviewed before you leave, and generally get aligned on!

In case that’s not simple and clear enough…I even made you a TEMPLATE:

The O’Daily: Parental Leave Planning Template

Obviously some important pre-work goes into this:

  1. Identify what you’re responsible for (more than you realize because #startups 😂)

  2. Figure out who can handle it while you’re out (let someone spread their wings!)

  3. Run it by your boss, the people handling items, their boss, etc. Get approval from all stakeholders.

  4. Highlight any major gaps in training, coverage, or resources and come up with a plan!

It’s usually 5-20 lines (aka “Items” that need coverage). More than that and you’re getting too granular.

For example, if you normally plan the company offsite, there may be 10 people who pitch in to help with different items but only 1 “who to ask/DRI” person on the doc.


3. Establish a communication plan.

Parental leave is not one-size-fits-all.

Hopefully someone asks you what you want but either way, spend some time thinking about how much and in what ways you want to stay up-to-speed on company happenings.

Your initial thought may be, “Not at all,” which is valid and possible in some roles.

But what if your manager leaves? What if the company has a major product pivot? What if they hire someone for your team? What if you’re the CEO or C-suite?

There may be certain decisions or items that come up so talking about when and how to reach out ahead of time can be helpful.

Your communication plan is a great item to add as Tab 2 on your ^^ Point-of-Contact Spreadsheet!

(Yes, it’s already included in the Parental Leave Planning Template!)

For example, here’s my plan from when I was a startup COO and took 12 weeks:

  • Company weekly update email sent to my personal email

  • Work email stayed active with a parental leave OOO but I turned off notifications

  • Signed out of Slack

  • CEO or team members would text me if something was urgent or important

I think I might have gotten 1 text about a password/login issue and the CEO called me about hiring a Chief Customer Officer (who I had already met and was awesome). Perfect!

Everyone was very respectful and never took advantage.

If you want to stay more involved, be clear about decision making and communication expectations. (Tbh - these are always good to be clear on, even without a baby!)

Clarify communication and decision questions like:

  • What decisions can the team make, what do you need to decide?

  • How quickly will you respond?

  • What channels will you respond on?

  • If no response, should the team wait or do what they think is best?

NOTE: You have to follow your own protocol! If you say, I’m not checking email but then you reply to email, that’s confusing. Then people will email you and expect you to reply. And you’ll be like, why is no one respecting the plan?? And then you have to look in the mirror and say, oops, and do a reset. 😁


4. Implement your plan before you’re out.

Remember that awesome spreadsheet of who does what while you’re out?

Start it several weeks before you plan to be out!

  • Dress rehearsal! Starting early lets everyone practice, ask questions, figure out where the gaps or sticking points are before you’re unavailable.

  • Unknown timeline. Babies arrive when they want to. Sometimes early, sometimes late. So let’s just go ahead and plan for early so we’re pleasantly surprised if you’re around for longer.

  • Calm before the storm. Expecting a baby whether you’re growing one, someone close to you is, or you’re adopting is busy and exhausting work. What better way to give yourself a teeny tiny respite by handing things off a little bit ahead? It’s smart for the business, for your own health and wellbeing, and for the baby! Being stressed out of your mind is not the ideal way to welcome a child into the world — though it’s happened many a time and turns out fine! 😉


BONUS: Standard Operating Procedure Template

Jacey Cadet is our incredible VP of Marketing and Community at Atlanta Ventures — who just had a baby!!!!!!!!

LOOK AT THIS CUTENESS 😍😍😍😍😍😍😍😍

Jacey was already an organization and process power house so this wasn’t “new” for leave but rather her normal MO.

Every event, podcast, newsletter, social post, or any other thing we’ve done 1 or more times, has a Standard Operating Procedure (SOP) doc.

She kindly shared her Standard Operating Procedure Template knowing I was writing on this topic!!

Steps, tools, timeline, copy, images, everything you could possibly want all in one doc or folder.

This is great for known and recurring activities especially with multiple stakeholders.

As I mentioned before, some startup tasks or projects are too “one-off”, evolving, or even unknown, to document. Then your best option is to train at least 1 person, ideally 2, on the basics and let them run with it from there!


Plan well but don’t go crazy.

Yes, you want to do a reasonable job of preparing others and covering your responsibilities.

But it’s a startup, people!!!!

There’s no way to cover every possible scenario when things change so quickly and everything is an edge case.

And if your company is doing it right, there are good people around you who will do a great job while you’re out! (If there aren’t, that’s another issue, unrelated to parental leave. 🥴)

So do your prep work and then let go.

With babies and startups, you can only control so much.

Let the fun and joy of the adventure unfold!


What’s your best advice, resource or tool for expecting parents to prepare for leave? What worked well for you? What was the most helpful advice you received?

March 5, 2024
Feb
27
7
min

5 Free & Low-Cost Ways Startups Can (& Should!) Support New Parents

Your team is small and cash is tight. But you KNOW that supporting new parents is important to you. Here are the top 5 things you can do to support new parents that are within any startup budget!

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Your team is small and cash is tight.

But you KNOW that supporting new parents is important.

It’s great for:

  • Retention

  • Recruiting and competing with other companies for talent

  • Showing employees that you care about them as a whole person

  • Doing the right thing in the world

  • Having more cute babies on the planet

  • Furthering humanity (yay procreation!)

It’s especially top of mind right now since not one but TWO women in the Atlanta Ventures family are expecting. Wooooooo!!!!!

This is the first of a few posts all about parental leave at startups — how to do it right even when teams are small and budgets are tight.

We’re gonna start with FREE (and low cost) ideas to support new parents!

Available to any company regardless of size or budget.

Here are the top 5 things you can do to support new parents that are within any startup budget!


1. Ask What They Want

Start with a conversation. So simple yet so often missed.

  • How can we support you?

  • What are you envisioning post-baby?

  • What matters to you most?

Don’t assume you know what someone wants or what the right thing is for them!

I know some parents (including birthing mothers) who don’t like to be out of touch for long. It’s more stressful to not know what’s going on than to be reading work emails during a 3am feeding.

This was not me :) I can’t turn off my brain if I see communication coming through. So I had a plan to get weekly updates sent to my personal email. Anything urgent or need-to-know was a text.

With some families, they want to stagger time off. So one parent will go back to work right away but then take time off for caretaking when the other parent goes back.

Others want all hands on deck or don’t have childcare secured yet.

Some parents would rather have a little time off before the baby is born. Others want to be distracted or get as much done before as possible.

And of course — the plan may change!

Just like with startups…whatever is planned, expect it to change!

Life, especially when babies are involved, is unpredictable. Parents may want something different than they thought. Or medical circumstances may require it. Or childcare plans fall through.

Ask questions to understand what kind of support someone needs and keep the conversation open!

#PROTIP
Working with a first-time parent who may not know what they need??
**Understand how they like to operate when on PTO — this may translate
**Help them get advice from other working parents (make an intro if you can!)


2. Flexibility

Don’t have a parental leave policy yet?

What you DO have is unlimited flexibility.

Lean into your startup strength.

You can offer parents with new little ones completely free but incredibly helpful options like:

  • Flexible work hours: doing 6a-2p, planning the day around naps, wrapping up after baby bedtime

  • Flexible work locations: remote, less in-office, or less travel

  • Flexible working days: a MWF schedule can be a lifesaver — especially if it’s early or the childcare plan hasn’t kicked in (daycare waitlists, amirite??)

  • Flexible about video turned on: being able to pump, nurse, feed, or hold a baby while on a call, not having to be showered or have spit-up free professional clothes on can be huge stress reliever

  • Flexible availability: folks who replied 24/7 pre-baby may not be instant responders anymore. A system for urgent items or getting aligned on internal response time expectations can be helpful.

  • Flexible overall: General kindness and grace go a long way. Missing a meeting, an emotional outburst, or unexpected doctor trip are all normal during the busy, adjusting season of new babyhood. Everyone remembers when someone is kind (or not).

#PROTIP
It make take a little time to figure out a new schedule and prioritization strategy but good performers pre-baby will be good performers post-baby!


3. Diapers and Meals

Not free but very low cost in the grand scheme of things.

Q: Do you know what you pay a recruiter to replace a senior level role?
A: $30,000

Q: Do you know what 3 months of diapers cost?
A: $400

(Yes, welcome to the pain of the diaper budget, my non-parent friends. Also, Peachies is an awesome EU diaper brand from an Atlanta-native founder!)

Q: How about 2 meals per week for the first 2 months back at work?
A: $600

(Doordash or Cookonnect are two options. Cookonnect is from an Atlanta founder!)

Q: Do you know how much goodwill you create with these small gestures?
A: Infinite.

People always remember how you treat them when they’re at their most vulnerable and overwhelmed. And their spouses do too!

Seemingly small items can create an outsized impact in decreasing stress, increasing wellbeing, and solidifying lifelong loyalty.

Especially if they are things that make the transition back to work easier.

If you really don’t have a couple hundred dollars in the company budget, what about setting up a meal train?

Free.99 baby!!!

#PROTIP
Meals when someone starts back to work can be even MORE helpful than meals when the baby is first born. The first few weeks and months of adjusting to a new baby while working can be a lot! Saving an hour or two in the evening is huge.


4. Interns, Contractors, Consultants

Interns are amazing. Best value in all of Startupland!!!

Can you hire an intern to help with tasks while someone is out or to help with workload as they return?

(Related: 7 Steps To Find (& Win) Outstanding Startup Interns)

Talk about it ahead of time so the intern can join 3-6 months earlier to ramp and learn.

When someone is on parental leave is also a great time to try out a consultant or contractor. There’s a natural end date, and if they are great, you’ll know for the future.

This is not free, per se, but it’s cheaper than:

  • hiring another person full time

  • recruiting, training, ramping a new person for this role because you alienated your current employee by overwhelming them while they had a newborn!

#PROTIP
Discerning between “absolutely required for our business to run” and “things that can be paused for now” is helpful in understanding cost and coverage needs when someone is out. If you initiate the must-have vs need-to-have conversation as a boss, it means a lot!

Will you need to initiative this convo? Here are tips on having a prioritization conversation with your boss.


5. Lactation Room

If you have a lactating parent at your company, you should have a lactation room option upon their return!

Someone may or may not be pumping at work but having a plan before they goes out is one less stressor and shows that you “get it” and want to support them.

What To Include:

  • Comfy chair

  • Table (for pumping supplies and/or laptop)

  • Door that locks

  • Fridge

  • Electrical socket

  • Ideally a sink

  • Window/door coverings (hopefully obvious?)

I’ll never forget a tour I took of a different co-working space and was like, where’s the lactation room? I received a blank stare from the man who had just spent millions on a build out, included lots of fun stuff, but had no wellness or parental infrastructure.

(Lactation rooms are sometimes general wellness rooms which can also be used for Muslim prayer times, meditation, etc.)

Needless to say, we didn’t move in there.

Revenue lost.

But not for your company.

BECAUSE YOU’RE GOING TO BE THE BEST PLACE FOR NEW PARENTS (even if you can’t offer 6 months of leave like Salesforce)!!

#PROTIP
If you need inspo, Atlanta Tech Village has a Lactation Lounge sponsored by The Mom Project, featured here. It’s amazing!


I’ll leave you with a final thought and overarching philosophy about parental leave.

The Mom Project Founder, Allison Robinson, told new parents:

“Give yourself grace, it’s a long game.”

This applies to employers and employees too.

Treating people well when they have big changes in their personal life pays for itself long term.

Be kind, ask questions, and win the long game.


What are your best suggestions for free or low cost ways startups can support new parents on their team??


Want more on this topic????

In the next few weeks, we’ll cover:
1. how to prep if you’re the one going out on leave
2. best practices and what a good parental leave policy looks like for a startup

February 27, 2024
Feb
20
4
min

3 Customer Success Strategies I Wish I Knew As A Newbie

Here are the 3 concepts that I WISH I knew when I started in customer success and you can learn today!

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We figured out a lot of helpful strategies in the trenches of customer success.

The most important — unbeknownst to us at the time — was to actually care.

Being kind and polite was another.

It’s shocking how many companies miss on this!

Empathy and genuinely wanting to help customers can be the difference in someone sticking with you after a few hiccups versus leaving for a well-funded, larger, more mature competitor.

Saying you’re sorry, being a friendly human, or responding quickly — even if it’s just to say you got their note and you’re looking into it — can set the stage for trust and long term partnership.

Our processes were strong.

We figured out strategies for successfully implementing customers, getting users on the phone, having productive check-in calls, training new team members, and more.

But there’s a lot we could have done better!

If I had maxed out my Customer Success skills in my 20s…HOW TERRIBLE. Mostly for customers everywhere 😂😂😂

But also for the evolution of tech companies and my own development and perspective on the world.

Here are the 3 concepts that I WISH I knew when I started in customer success and you can learn today!


1. Ask About The Pain, Not The Product

We used customer check-in calls to ask users for product feedback.

What features would you like to see?
What things in the app do you like/dislike?
Did you know about this great new feature we have!?!

A combination of working with product visionaries like Billy Hoffman and reading books like The Mom Test, made me realize the product is secondary.

The user and their pain is #1!

Asking more about the person’s objectives, goals, job focus, and daily pain points.

What are you trying to accomplish? Why?
What keeps you up at night?
What’s the hardest part of your day?

Imagine the feedback you gather asking those questions instead of “product feedback!”

Yes, talking to customers in any format is the most important thing.

But asking high level questions — without your product as the focus — can transform the depth and quality of insights. Your customer relationship moves from transactional to a true collaboration.

Ironically, when you don’t talk about the product, it makes your product stronger in the long run!


2. Align To The Customer’s North Star

And speaking of product…it’s hard not to be obsessed with your company’s software.

You’re using it all day, everyone around you is too, you’re deep diving into customer usage and support tickets, you see new features in your dreams!

You want customers to be happy and they do that by using your product to the max!

We said a lot of things like:

They should use A/B testing with their landing pages!
If they had more users, it would be stickier. Let’s offer a training.
Why don’t they set up more website checks? They have 2 more in their package.

Customers win when they use more of our product.

Right?!?

Except to the customer, your product is just a tool. A means to an end.

They care about something much bigger.

AND YOU NEED TO KNOW WHAT THAT IS!!!!!!

What do your users get measured on?
What is the business model of your customer’s company?
What is the #1 responsibility of your executive buyer at their company?
Why does your power user get promoted? How is their job performance measured?

THESE are the North Stars, a transformational concept I learned from the brilliant Francis Cordón.

This is what you should talk about on a call, showcase in a product dashboard, and align to internally!

Forget about product usage or CSAT. (I mean, it’s still helpful in certain contexts but not the end goal…) Figure out what your customer’s North Star is and track that to measure your success!


3. Reach Out With A Customer Win

Yes, you can get customers to talk to you.

You can look at their account and review call notes to prepare relevant talking points.

We offered account audits (100% manual process of assessing and compiling…) to highlight where a customer could find more value in the tool.

All of this is great.

But IMAGINE if I had reached out proactively with a Customer Win (another concept from Francis Cordon!).

The email would go something like this:

Hey Customer Friend,
Look at this amazing quantitative result that I found in your account that aligns with your North Star. I put it in an easy-to-digest, one-page visual format. Now you can forward this to your boss who can forward to their boss. You look incredible and might even get promoted because of us!

Your Fave Customer Success Person Ever,
Kathryn

I predict a 100% response rate with 100% customer retention 😁

Okay, obviously, you wouldn’t be able to find that style of win for every single user, but how impactful is it to come at Customer Success from that perspective??

Outta here product feedback. Let me help you find wins to share.


What is a Customer Success strategy you wish you knew when you started? Any experience with these tactics or others? Who is someone you learned from??

February 20, 2024
Feb
13
5
min

5 Tips For A Phenomenal Customer Check-In Call

Customer feedback is the lifeblood of every business! I’ve made 1000s of customer check-in calls over the years. Here are my 5 top tips to maximize your time with valuable customers!

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Customer feedback is the lifeblood of every business!

If you get a customer to talk to you (after using these tips), you want to make the experience helpful and positive for them and you.

I’ve made 1000s of customer check-in calls over the years.

Here are my 5 top tips to nail your customer check-in call and make the most of your time and the customer’s!


1. Schedule The Call…& Follow Through

Rule #1 of customer calls is you must actually get the customer to talk to you. Harder than it looks when you’re talking about busy professionals.

Detailed HERE but my team and I had good success with these steps:
1. Send an email to schedule a call
2. If no reply, send second email with tentative calendar invite when I’ll call them
3. Call them at that time
4. If no response, send follow up email with info
5. Try again next quarter (tweak the message and strategy)

And substitute “Zoom” or “Google Meet” for “call” since things changed a bit in 2020.


2. Talk (At Least) Quarterly

As the first “Client Advocate” (now called Customer Success Manager) at Pardot, I did monthly customer calls.

We were a month-to-month SaaS subscription, no contract. We needed to win your business every month!

I quickly learned that monthly was too often. Not enough changed in the product or in their business to have a valuable call every month.

Quarterly it was!

Note: We were early (<100 customers) but the product was built and I was talking to customers who were up and running successfully. In maintenance mode, if you will. I recommend weekly calls for implementing new customers.

If you’re in the “design partner” stage or very early, monthly or weekly or twice weekly might be best.

If you’re fairly established, quarterly is great. Even if Especially if you are on annual contracts, you want to talk to your customers quarterly.

Nothing says, “You don’t matter at all” like calling 1x per year right before renewal. 🥴

Talking quarterly also gives you time to “save” an unhappy customer.

By the time they want to cancel, it’s too late.

If you talk to them 6 months before, you can proactively address concerns, fix bugs, share roadmap, sell to new stakeholders, offer additional training, re-implement, and 100 other churn busting strategies!

Yes, when you have thousands of customers, you will need to segment customers and scale your programs.

But if you’re B2B SaaS or at a deer or elephant price point with <1000 customers, call every quarter.


3. Prep Accordingly

Deliver a great experience to the customer by being well-prepared!

  • This implementation prep guide also applies to customer check-in calls!

  • Use Zinnia Daily to get user and company bios delivered to your inbox.

  • Understand what their North Star is!

    • What product usage can support this?

    • Any new, unused, or upcoming features that further their North Star?

  • If you can, review their account data, what features they’re using, uncover customer wins, and look back on previous calls.


4. Create A Framework For Taking Notes

If a call goes well, it’s going to be a firehose of info! Hopefully some follow up items too.

That’s great.

But hard to keep track of.

Do NOT take notes chronologically as someone talks on the call.

INSTEAD: start with a list of categories and drop items into each section as they come up.

Why A Notes Framework Is Awesome

  1. You easily remember and cover main topics

  2. Your call notes are ready to save/share

  3. You can quickly send follow up (and even a call recap to the customer!)

  4. Everyone on the team can follow a similar format

**Thank you Nicole Bradshaw who taught me this!

Example Notes Framework

  • Next Steps

  • What They Love

  • Pain Points

  • Other

Example Notes Framework - After Call

  • Next Steps

    • Intro: Product Manager

    • Send article: forms best practices

    • Follow up: support ticket on spam

  • What They Love

    • Improved open rate

    • Email segmentation

  • Pain Points

    • Email testing

    • Slow response time on ticket

  • Other

    • Attending user conf!


5. End The Call With A "Scale of 1-10" Question

If a call goes well, a customer is going to tell you all sorts of feature ideas, things that suck about your product, and ways you can improve as a company.

The customer is going to feel great. You will feel terrible.

You’ll be like, they’re going to cancel. They hate us.

THAT’S WHY SCALE OF 1-10 IS CRUCIAL.

Towards the end of the call — after listening, discussing, taking notes on all the constructive feedback — ask this question:

Scale of 1-10, how happy are you with <OurCompany>?

Variations include:

Scale of 1-10, how are you guys doing?
Scale of 1-10, how easy is it to use our product? (because I love Customer Effort Score)

You can also ask straight up NPS (How likely are you to recommend us?) or CSAT (How satisfied are you?) but most customers know those and they sound a little canned.

The goal is to get a quantitative temperature check and have a (semi-reliable) number for reference in your notes.

Sometimes people with the most product feedback are wildly happy. Sometimes they hate you. It’s hard to know until you hear a number.


So that’s what we got right.

Guess what…made some mistakes too 😉

Tune in next week for 3 Customer Success Strategies I Wish I Knew As A Newbie!


What are your best strategies for gathering customer feedback or conducting customer check-in calls?

February 13, 2024
Feb
6
4
min

4 Steps To Get Customers On The Phone – Even When They Ghost You 👻

How do you deliver a great customer experience? You talk to customers!!!!! That said, having conducted 1000s of customer check-in calls, sometimes the hardest part is actually getting customers on the phone (or Zoom)! Here is my 4 step strategy to getting (most) customers to talk to you.

Read More

How do you deliver a great customer experience?

You talk to customers!!!!!

No tricks or shortcuts. MUST. TALK. TO. HUMANS.

Their unvarnished input, ideas, perspectives, and problems are mission critical to success.

That said, having conducted 1000s of customer check-in calls, sometimes the hardest part is actually getting customers on the phone (or Zoom)!

Here is my 4 step strategy to getting (most) customers to talk to you.


1. Send The First Email

Most people appreciate a heads up and unless you’re on a texting basis with a customer, email is the best first touch point.

  • Send an email saying that you’d love to hear how things are going and get their product and company feedback. People don’t like to answer a bunch of questions. They LOVE to share feedback though.

  • Other messaging to test with your customers

    • New features

    • Product roadmap

    • Be a case study

    • Account audit

    • Ask for their “help” (people love to help, it’s a trigger to say yes)

    • Offer help with a certain feature or tool setup that you know applies to them

    • Links to helpful resources (this can backfire…“I read the links, I’m good.”)

  • Position it as 10-15 minute call. Short and manageable.

  • Include a scheduling link (we like Calendly for obvious reasons 😉 ) and some times listed out. Don’t make them click into a link if they don’t want to.

  • Use their name, company name, and a personal detail if you can. No one will reply to an email blast or generic email (unless they are angry!)

  • Short and sweet! Now take out all the extra words. Mo Bunnell gives great tips on business development emails that also apply here.


2. Send A Second Email + Cal Invite

Your best and favorite customers will probably reply to your first email.

Most won’t.

That’s okay! They’re busy.

It’s probably a good sign that your product is not a hair-on-fire problem for them 😂

But you still want to talk to them!

Here’s what you do next…

Send a second email like this one:

I know you’re busy dominating marketing campaigns :) I’ll give you a try at 404-911-9111 tomorrow at 3p. I’ll optimistically send over a calendar invite but let me know if something else works!

Key details:

  • “optimistically” or “tentatively” seems to be a key word — makes it friendly instead of pushy

  • reply to/thread with the first email so they have context of your previous email

  • CALENDAR INVITE!!!!! Send over an invite as soon as you send your email. Include your name/company, their name/company, and a bit of context. So if they haven’t read your email and see the calendar invite, they know what’s going on.

I SWEAR this email has a 50% reply rate.

People will say:

  • Great, talk to you then.

  • How about at 2:30p instead of 3p?

  • Use this # I’ll be in my car.

  • Let’s do the same time but next week.

Or sometimes it will be things like:

  • Fine, no need for a call

  • Too busy to chat but we’re good

  • We’re switching to a competitor (ouch!)

But at least you’re getting info!

Fun fact: I got this strategy straight from a sales person.

What’s aggressive in sales is helpful and proactive with customer success! 💖 🙌 😁


3. Call Them Anyway

First and foremost, I absolutely, positively, definitely call them (or get on the Zoom) at the time I said. Even if they don’t reply.

You’ll get at least another 10-15% of folks who don’t respond but answer the phone or show up to a virtual meeting.

If I get 🦗crickets🦗 and no engagement, at the very least, it’s already on the calendar (Productivity Starter Pack Tip #2) so I’m accountable and have time to follow up.

Which leads me to…


4. Leave A Message & Send Another Email

The best laid (customer outreach) plans don’t work for everyone.

Use your calendar block to:

  • Leave a friendly message

    • Intro yourself, obvi

    • Indicate you’ll also send an email

    • Feel free to include 1 short tip, new feature, upcoming event they might like

  • Send a follow up email

    • BEFORE your goal was to talk to them

    • NOW — you want to share helpful info via email

    • Bullets, hyperlinks, still keep it as short as possible (3, maybe 4 bullets)

    • Customized to their account/usage/goals if possible

Even if we don’t talk this time, I build trust with follow through!

Make sure to include a Calendly link and open invite to chat when the time is right.


Next Time…

You never know what’s going on when someone doesn’t reply.

Here are real examples why a customer went dark:

  • 6 month struggle with Lyme disease

  • 7 tradeshows back-to-back

  • On vaycay!

  • Getting married

  • About to get fired

  • Testing a competitor’s product 🙃

  • Huge internal project/launch

  • Inbox overload

  • Prefers in-person

And 100 other things.

So if at first you don’t succeed, try, try again!

Run your outreach playbook again next month or next quarter depending on the customer, your company size, and what seems reasonable without being annoying.

Figure out what works with your unique customer (at Rigor, engineers hated phone calls but loved email and chat!) and test new strategies, language, and resources.


What are your best strategies for gathering customer feedback? Any tips for getting busy customers to talk to you?

February 6, 2024
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