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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 By the time you update documentation, it’s out of date.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.


  • 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!!!!!!!!


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

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!

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).

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!!!

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!

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)!!

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

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.


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

They care about something much bigger.


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,

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

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.


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

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.

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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

How to Break into Tech...Or Find New Role in the Biz

Check out these 4 strategies + 1 bonus tip (from a career transition expert) for getting into tech!

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Raise your hand if you know at least one person trying to “get into tech”!


For the 99% of O’Daily readers that already work in tech, you can either:

  1. Forward this article to that friend, family member, or distant LinkedIn connection who asked you how to break into tech without a tech background… then get back to your tech job with renewed appreciation for work satisfaction and free snacks.

  2. Read on for strategies that also apply to “breaking into” a new role, industry, department, or favorite startup.

After you’ve read the rules of finding your startup dream job, check out these 4 strategies + 1 bonus tip (from a career transition expert) for getting into tech!

1. Warm Intro (& How I Got My First Tech Job)

Find a friend at a tech company!

Most companies give referral bonuses so don’t feel bad about reaching out.

Going through a real human means you’ll at least get your resume looked at with fresh eyes and the benefit of the doubt.

At some places, any referral from a current employee automatically gets a phone interview.

Many startups will take a bet on a smart, positive generalist (as does Amazon and Google) especially for roles like customer success, support, or sales.

But you WILL need someone to vouch for you since your resume will look similar to 100s of others so find that person who can refer you!

Here’s my story:

Three years out of college, recently back in my hometown of Atlanta, doing a job search, I ran into a high school friend at a party.

Bradley Wagner (19 years as VP Engineering at Hannon Hill!) heard about my job hunt and mentioned they were hiring at Hannon Hill and other incubating companies (ahem, Pardot).

I sent my resume over the next day...

as a liberal arts Spanish major with 2 years experience in non-profit fundraising. 😂😂😂😂

With an internal referral, I got a call from Jamie-in-HR which converted to an in-person interview.

I regurgitated enough tech talk (learned through lots of Googling) they were willing to take a chance on me.

Fast forward a few technical challenges, lots of learning, and a very lucky rocketship ride later…I’m Tech4Life, baby!!

With new technology, no “experts” exist yet! Current “AI experts” only have 1-2 years under their belt. Don’t be intimidated by not knowing a new tech product. High growth, innovative companies value learning, thinking, and problem solving more than product expertise.

2. Start Doing Tech NOW!

Same advice that I give folks who want a promotion:

Start doing the job you want today. Build the skills and track record. A promotion (or tech role!) becomes a no-brainer.

Here’s how to do a tech job today (even if you don’t have one):

  • Lead a software or tech tool implementation for your current company

  • Become a power user of your company’s tech tools

  • Bonus points: Train co-workers to be power users too!

  • Get really good at freely available tech like social platforms, ChatGPT, wi-fi enabled house gadgets

  • Offer to help a solopreneur build a website, edit video, or other tech task; learn as you go!

  • Apprentice with the owner of a small tech-related business or barter your expertise for training on theirs

  • Explore TalentStacker and get Salesforce Admin certified

  • Figure out ways to make your current job better with tech (even if you’re the only one using it)

Why it works:

  • You gain confidence in your own tech (and learning) skills

  • You may find a more technical role within your current company

  • You are building your tech-stories-to-talk-about-in-an-interview repository

  • You learn the lingo

All of which…can be used in your resume and tech job search!


In addition to any tech projects, make sure you highlight relevant and transferrable skills on your resume! Don’t assume a hiring manager or recruiter will connect the dots.

Customer service, project management, event planning, training others…all of these are relevant to tech companies.

Remember — if you can use Snapchat/Facebook/Instagram/Tiktok, you can use a CRM. 😂

3. Look For Tech Companies In Your Current Space

Working at a restaurant? Look for restaurant tech companies.
Working in fashion? Look at ecommerce or fashtech companies.
Working at a law firm? There’s tons of legal startups.

(How to find tech companies? Check out Tips 1, 2, 4 from 7 Ways To Find Your Startup Dream Job.)

You may not have tech experience but you have industry experience — which can be extremely valuable, especially at early stage startups who know tech but not the industry.

Don’t love the industry? That’s okay!

Step 1: Get a tech job in your current industry.
Step 2: Now that you have tech experience…get a tech job in another industry.

Much easier to change one thing at a time than both at once.

What kind of role should I look for?

Align with your current skill set but when in doubt, customer success is a great starting place!

  • With industry expertise, you know the customer, pain points, and lingo.

  • You don’t have to be super duper techie. Just more techie than the customer! (Plus there will be help articles and training resources.)

  • Not excited about customer support forever? It’s a great training ground and jumping off point for sales, engineering, product, and marketing roles.

Love to sell? Great at writing and social media? Marketing or sales is another good “generalist” area, especially with industry expertise.

If you find an aligned company with no open roles…reach out anyway! Companies may hire opportunistically or may have a job coming open soon.

4. Hang Around Tech

Don’t know anyone in tech? Or maybe you *think* you want to do something in tech but need more data?

Check out these events, groups, and suggestions for getting connected in the Atlanta Tech scene.

Not from The A? I’ll bet someone has a similar list for your city. (Share in comments if you know of one!👇)

Alternatively, find some local tech folks on LinkedIn and see what events they’re going to or ask them for suggestions.

Being a helpful, kind, regular participant is noticed and appreciated.

Thank the event hosts, post on social, and before long…trust is built and people assume you’re already in tech!

Easy to get intros or start conversations from there!

No time to network?

Atlanta Startup Convos and Atlanta Healthcare Entrepreneur Meetup are both virtual!

Or find something like Pitch and Run where you do a thing you were going to do anyway (exercise) while networking.

BONUS: Wicked vs Kind Environments

I asked Margaret Weniger, who has spoken to 100s of women about career transitions, for her advice. She shared this insightful perspective on identifying where you thrive!

Psychologist Robin Hogarth was the first to articulate two types of learning environments, wicked and kind.

Kind Environments

  • Patterns repeat again and again.

  • Feedback is rapid and accurate.

  • A learner can improve simply by engaging in the environment.

  • Chess is a great example or a mature tech company with an established playbook.

  • Narrow specialization is highly valuable in kind environments.

Wicked Environments

  • The rules of the game are often unclear or incomplete.

  • May or may not be repetitive patterns that can help inform decisions.

  • Feedback is often delayed, inaccurate, or both.

  • More likely found at early stage companies and startups.

  • Breadth of experience is valuable in wicked environments.

When you think about breaking into tech, consider if you want a wicked or kind environment!

Startups are “wicked” where you are often tasked with a project or problem with minimal resources or guidance. Asking questions, running rapid tests, and a bias for action are highly valuable skills. 

Late stage and larger tech companies will be “kinder” with more guidance, predictability, and repeatability.

Let this not be confused with the humans and the culture, which can be kind (or wicked 😈) at any size company!

What’s your best advice for breaking into tech? If you crossed the chasm to a tech job, what is your story??

January 30, 2024

5 Resources to Help You Nail Your Pitch

Here are 5 great resources to help you with your pitch — the deck, the speaking, the story — all of it!

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A pitch deck is like your dating profile.

You want it to highlight the positives, show why you’re a winner, and be visually pleasing. All without overselling, which would damage relationship trust before it starts.

And the pitch meeting itself is a first date.

There was enough alignment and intrigue on both sides to be worth a meeting.

You want to see how the real humans hold up compared to the digital story.

Could this be a fit?

There’s still a lot to learn about each other, you expect some of the shine to wear off, but if there’s no red flags or misalignments on timing, goals, key milestones, stage on either side, both sides will proceed with optimism and caution!

Sounds so easy when I put it like that. LOLOLOLOL.

Anyone who has put together a pitch deck, presentation, resume (or dating profile? 😂), knows that it’s 100x harder than it looks. The ones that look “effortless” are likely the result of hours and hours of agonizing.

What’s relevant, how to tell the story, how to customize, what the audience cares about, the data to include…oh and now cut it down by 50% and simplify everything!

If this is resonating…I hear you and I want to help.

Here are 5 great resources to help you with your pitch — the deck, the speaking, the story — all of it!

1. Pitch Practice

  • Weekly at the Atlanta Tech Village (ATV) — 9 years running!

  • Led by Jacey Cadet who excels at storytelling, design, and friendly feedback

  • If you’re a member at the ATV, you also have access to Mentors & Advisors who will bring their unique expertise (marketing, pitching, sales) to a 1:1 meeting.

2. First Pitch Friday

  • Monthly event for female founders (May - August) & student founders (September - April)

  • Live pitch experience and on-the-spot feedback from VC investors

  • Led by Allyson Eman and Christy Brown

3. Dedicated Coach

Here are 3 that I know personally and come highly recommended from founders to help with your pitch, fundraising process, and sales strategies!

4. The O’Daily 😉

Yep, we’ve talked about how to pitch (with more to come)!

I also love Dave Payne’s advice and Step-by-Step Fundraising Tactics from the NYC Legend Who Raised $750M from First Round Review.

The Atlanta Ventures blog is also a wealth of pitch info!

5. Feedback Fridays

What are your favorite pitch resources? They can be blogs, templates, tools, events, or humans!

January 23, 2024

SaaS Masterclass: 3 Top SaaS Thought Leaders & Their Best Blog Posts

2024 is the year the O’Daily gets SaaSy. Here a 3 great SaaS thought leaders with 3 of the top articles from each.

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I made a terrible mistake last year.

Ironically (or idiotically?), I rarely posted about B2B SaaS.

Even though I have 15+ years of experience scaling B2B SaaS companies.

I made the classic startup mistake where you forget — or don’t realize — how much you learn along the way!

Well, folks, this egregious oversight ends today.

2024 is the year the O’Daily gets SaaSy.

(Not to be confused with “sassy” which we’ve been for years. 😂 💃)

Starting with some of my favorite SaaS thought leaders and the content we referenced most often from the trenches!

Here a 3 great SaaS thought leaders with 3 of the top articles from each.

1. Jason Lemkin via Saastr

What started as an awesome blog by Jason Lemkin, founder of EchoSign, is now a world-wide sen-SaaS-tion!

The SaaStr Annual conference is excellent! I attended and loved it. Relevant, actionable content and tons of SaaS founders, leaders, and investors who “get” it.

2. David Sacks

Ex-Paypal, founder of Yammer (acquired by Microsoft) who started Craft Ventures that invests exclusively in B2B SaaS. He’s a no-BS, numbers-oriented dude who has seen a tons and knows the playbook (and pitfalls!).

Hear David Sacks’ current insights on SaaS, tech, and business every week on the All-In Podcast which is one of my favorite podcasts and a great way to understand how VCs think!

3. David Cummings

DISCLAIMER: I was part of two successful SaaS companies that David founded and invested in. Oh, and he founded Atlanta Ventures where I’m a partner now!

He’s written over 3000 (!!??🤯) blog posts on entrepreneurship and built multiple successful SaaS companies, so yeah, he’s a great resource!

One of the best behind-the-scenes look at the early years of a now-multi-billion dollar SaaS company with David and Kyle Porter talking shop (as yours truly moderates).

What are some of your favorite SaaS articles or thought leaders? What resources do you reference frequently?

January 16, 2024

4 VC-Approved Tips to Make Your Startup Irresistible

Happy Fundraise Kickoff! Here’s 4 ways to align your company and positioning so a VC can easily say yes.

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Happy New Year Fundraise Kickoff!

Holidays are over which means…

Investors are back in the saddle, ready to kick ass and write checks!

(ICYMI - Winter break and summer are notoriously slow in fundraising land.)

If you’re a founder getting ready to raise — especially if you’re new to the world of venture capital — here’s what is often misunderstood:

VCs have bosses.

They have to show returns on the money they invest.

Money that belongs to someone else.

Money that comes from:

  • Non-profits

  • Hospitals

  • Pension funds

  • Higher ed institutions

  • Family offices

These institutions are expecting financial returns so they can support things like sick kids, scientific research, workers in retirement, and the next generation of thinkers and leaders.

So even if you’re talking to the founding partner of a firm — who seems like a successful, high roller — they are answerable to their “bosses”, they’ve set certain expectations about what and how they’ll invest, and they feel tremendous responsibility to generate returns.

Why does this matter????

It’s important to understand so you can position your business accordingly!

Many VCs care deeply about the world, helping others, doing good.

But they can’t say yes to your company if the likelihood of a large return is not there.

So…make it easy for them to say yes!!!

Here’s 4 ways to align your company and positioning so a VC can easily say “Yes To The Dress Invest!”

1. Pick a big market.

Big market = big returns. An amazing founder or idea in a small market can never deliver big returns. (Which I talk about in detail here and here!)

So even if a VC loves you, if the market is too small, they will pass.

Related — make sure you clearly and realistically explain your TAM SAM SOM. The more realistic the math, the more trust (and excitement) you build.

VCs can sniff out an exaggerated market quickly so don’t try to “check the box” on this.

2. Talk about the money!!!!!!!

The thing that hurts my heart the most?? A founder with traction and a great business model who doesn’t talk about it until the end of their pitch.


Do it early. Do it often. An investor’s (love) language is DOLLARS.

(See “VCs have to show returns” above. 😂)

No revenue yet? That’s okay! You can still use dollars and numbers to tell your story.

3. Understand the investment thesis.

Venture firms can vary wildly based on:

  • Stage

  • Check size

  • Types of companies they invest in (software, hardware, consumer products)

  • Types of industries

  • What they look for in a founder

  • Business model (transaction fees, recurring subscription)

  • Being a “Strategic”

Even partners within the firm may focus on different things.

So make sure you know who you’re talking to and that you’re highlighting what matters to their firm. Save your best for last so you get lots of practice!

Firms will very occasionally make exceptions to their investment thesis or criteria. But it’s usually for someone they’ve known for a long time or a company with insane traction.

4. Believe in yourself.

At the end of the day — especially in the early stages — investors are investing in YOU.

Your confidence, perseverance, creativity, intelligence, vision, ability to sell, and ambition to build a billion dollar company will attract others, including investors.

Confidence and belief are contagious — and vital for weathering the hard times that will inevitably come!

Yes, you need to be coachable and not a dickhead.

But the ability to inspire buy-in from employees, customers, and other investors is something that investors vet heavily.

Kevin Ryan has amazing examples and specific phrases about how this can look in “Step 2” of Step-by-Step Fundraising Tactics from the NYC Legend Who Raised $750M.

Not sure this is you?

The best, most successful CEOs weren’t sure either. They figured out ways to overcome their own doubts, including…

Fake it ‘til you make it!!!

You can also practice and be intentional to:

There’s compelling research that the most well-funded founders (regardless of gender) know how to redirect the conversation to talk about the vision and upside.

It’s a strategy that comes across as “confidence” but is actually something that can be cultivated and practiced!

Fundraising is a full-effort process that can take 100+ meetings to get the desired results.

Understanding what matters to VCs and how to best position your business can speed things up.

Want more tips on fundraising or how to work with investors? Check out these resources and reply below with future topics you’d like me to cover!

What’s your best tip for fundraising?? What should founders and startups know before “going out to market”?

January 9, 2024

1 Sentence You Need To Read Before The Holidays

I don’t know who needs this but I’ve seen a few startups fail from founder burnout. I haven’t seen any startups fail because a founder took a couple of days off.

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I don’t know who needs this but I’ve seen a few startups fail from founder burnout. I haven’t seen any startups fail because a founder took a couple of days off.

I love this advice from Alex Friedman (which is technically TWO sentences, you fact-checking, math geniuses!).

Wrap up the year, close the deal, get through key emails…and then close your laptop.

It is harder to take time off.

It takes more discipline, confidence, and focus to NOT work than to default to grind mode.

The difference between the elite and amateurs in triathlon (or any high level sport)?

How they handle the off-days.

Someone who is taking their rest seriously? Feet on the couch? Massage? Naps? Clearly a pro.

Someone who is sneaking in extra miles or saying, “I just can’t take time off” like a humble brag? Amateur hour.

Trust the process. Trust yourself.

I know you can do it!

Have an amazing holiday, pour into your loved ones, and can’t wait to hear how hard you relaxed.

See y’all in 2024 ready to DESTROMINATE!!!!!!!

December 19, 2023
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