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!!

#PROTIP
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!

#PROTIP

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.

#PROTIP
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!

#PROTIP
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??

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!

• Lauren Kane of VC Worthy

• Charlotte Ketelaar of ZWANET

• Margaret Weniger

4. The O’Daily 😉

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

• How To Talk About Revenue...When You Don't Have Any

• 4 Ways To Crush Your TAM/SAM/SOM

• Show Me The Money: #1 Tip For Pitching Investors

• 4 VC-Approved Tips to Make Your Startup Irresistible

• 6 Simple Ways To Build a Relationship With a VC

• Unexpected Fundraising Secrets From a VC

• 6 Ways to Think Like a VC

• 3 Strategies For Establishing Credibility — No Matter Who You Meet

• 6 Ways To Project Confidence Without Trying

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

• Every other Friday at ATDC on Georgia Tech campus

• Open to the community

• Led by Carnellia Asajin

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

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 48 Types of VP Sales. Make Deadly Sure You Hire the Right One.

  • Evangelist - Make It Repeatable - Go Big - Dashboards chart is legendary.

• From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase. But — The Cavalry is Coming.

  • Unending list of urgent priorities but no resources to address them? Correct! 🙃 But it does get better! (Circulated frequently at early Pardot 😂)

• Customer Success Is A Single Digit Hire - I may be biased (just a few articles on Customer Success on the O’Daily)…but Jason lays out the financials and experiences to back me up!

#PROTIP
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!).

• Simple Math To Set Up A Sales Team - base salaries, quotas, commission, CAC

• The Dark Side of Sales - 10 potential pitfalls of fast growing sales teams

• Key SaaS Metrics - what they are, how to calculate them

#PROTIP
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!

• 12 Ideas To Strengthen Culture - culture is the only sustainable advantage a founder has complete control over. No one is better on practical, actionable strategies for this than David.

• 4 Reasons for Startups to Avoid Big Partnerships - not talked about as much as it should be; check out the “related articles” for more tips on this.

• 5 Controllable Factors In The Pardot Success Story - applicable to your SaaS company too!

#PROTIP
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?

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.

PLEASE — for the love — TALK ABOUT THE MONEY!

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:

• build relationships with VCs

• project confidence

• establish credibility

• learn to sell (or improve and grow at anything)

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”?

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!!!!!!!

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!!!!!!!

Last week, I let you in on the biggest secret (or most helpful insight???) in the entrepreneur biz.

EVERYONE HAS IMPOSTER SYNDROME.

But you’d never know.

Why?

Because the best founders and leaders have figured out how to:

• Establish credibility
• Project confidence
• Proceed with courage and conviction…despite insecurities!

And there’s more.

I’ve been behind-the-scenes with hundreds of talented, wildly successful entrepreneurs.

Here are the 4 patterns I’ve seen from the best of the best.

Yes, even the best have self-doubt and worry — but they leverage these 4 truths to unleash their greatness!

1. Lean Into Strengths

Most CEOs, founders or leaders can tell you what they’re good at (and what they’re not good at!).

It will sound like this:

• I may not be able to code but I know I can sell.
• I love big meetings and being on stage but I suck at the financials.
• I’m great at strategy and vision (but bad on details).
• I’m good at figuring stuff out.

They know that you don’t have to be great at everything. They are insecure about their weaknesses but leverage their strengths to the max:

• I’m going to sell the shit out of this product so that I have enough revenue to hire a finance person who can help me.
• I’m going to listen to my customers and act on their feedback better than anyone else.
• I am great at prepping. I am nervous but well prepared.

EXPLORE: What are your strengths and how are you going to lean into them to build a big ass business??

2. Work On Weaknesses

Behind every great leader is…

• Executive coaching
• Peer accountability groups
• Professional development courses
• Tons of reading and learning

That polished stage presence?

It may be a result of a $10k exec training and 100 hours of practice.

Many skills including things like “confidence” and “sales skills” can be cultivated and learned.

EXPLORE: How are you systematically improving? Are you using support and accountability to accelerate the process? Here’s more ideas, resources, and founder stories.

3. Build Your Confidence Data Set

Think about your first pitch. Now think about your 50th pitch. Way better, right?

You have an important data point:

I used to suck but I practiced and now I’m much better. That means I can work on other things and get better too.

Every repetition builds on itself:
I am little more confident than last time because I’ve done this before. Because I’m more confident, I will do a little better and learn more new things that make me even better for next time.

What else have you done that you didn’t think you could?

What have you worked at?

What is easy now that took tons of effort at first?

How about…

• Learning to read
• Driving a car
• Living on your own
• Trying again after the first time didn’t work
• +100000 other things!

Even if you’re early in your career, you have plenty of examples.

Whenever you feel insecure, use your life resume as a confidence boost!

EXPLORE: What is a hard thing that you’ve done? What seemed impossible when you started but you got better over time? Make a list for reference! Ask a friend or loved one if you need perspective.

4. Ambition Means Insecurity

It’s the cooler, more positive side of the Peter Principle.

Someone who is ambitious will always feel a little out of their league.

Why?

Because they’re pushing out of their comfort zone to grow.

The best people never want to be the smartest in the room.

It’s a recipe for personal stagnation.

But the inevitable result of intentionally not being the smartest?

You always feel not-quite-as-smart.

Self-inflicted insecurity in the pursuit of improvement and greatness!

If I want to feel fast, I can race a slow person.

If I want to be fast, I run with people faster than me and get my ass kicked daily.

And — of course — with the most hilarious life irony — the faster I get, the more I understand how slow I am!

When I am at top speed, running all out as hard as I can, it’s still 2 minutes per mile (aka 50%) slower than the fastest marathoner in the world. Yes, the best runners can run for 26.2 miles at a 4:30 minute per mile pace and my 30 second sprint might hit 6 minutes.

The better you get…the more you understand how far you have to go!

Running is an easy analogy but of course this applies to company building, technical knowledge, sales, parenting, investing, EVERYTHING!

You don’t feel insecure because you’re not good. You feel “insecure” because you want to continually improve and be challenged!

EXPLORE: How have you challenged yourself recently? What “room” did you enter knowing it would be hard but a great growth opportunity?

What are the most important insights you’ve learned about doubt, confidence, and success? What are great leaders doing that we can all learn from? Do you agree that the more you learn, the more you realize how much you don’t know?

Every founder, entrepreneur, CEO I know…at some point…when their guard is down…has alluded to the fact that they:

• got lucky
• don’t know what they’re doing
• might not be the best person for the job
• are envious of someone who is “better” or “ahead” of them

Don’t believe me?

Here’s a peak behind closed doors:

• One of the most inspirational speakers I knew, who founded a company and took it public, got extremely nervous backstage before speaking!
• CEO who built a $10M ARR business said, “I don’t know what I’m doing. I hope no one finds out.” He was joking. But not really…
• Founder who built a $500k business in 6 months says, “I stumbled into this.”
• Miley Cyrus being nervous and listening to a Britney Spears song as her reassurance. (Also an early ‘00s banger. You’re welcome. )

This is not false humility.

These are incredibly successful humans who have doubts about themselves and their accomplishments.

So what’s their secret?

How do they overcome insecurities?

Here’s the thing — they don’t overcome them.

They do it anyway.

They don’t let the fear or doubt stop them.

They do the thing —customer meeting, public speech, company launch, capital raise— with conviction and courage despite their insecurity.

They lean into their strengths, work on their weaknesses, and act with confidence even if they don’t always feel it.

Why do I share this?

If you feel insecure, it’s NOT a sign that you can’t, shouldn’t, or don’t belong.

It’s a sign that you have big ambitions and you match the profile of a typical CEO.

Everyone feels insecure, including amazing people that you respect and admire.

They are doing it anyway.

And so can you.

What would happen if you DID IT ANYWAY???

What’s more important — how your customer feels about you or what their usage tells you?

It’s an age old question in customer experience.

Here’s how I think about it:

• Axis #1 = customer satisfaction (CSAT) - reported via survey
• Axis #2 = customer usage - reported from within the product
• Which creates 4 quadrants:
• High CSAT, High Usage
• High CSAT, Low Usage
• Low CSAT, High Usage
• Low CSAT, Low Usage

You can then prioritize and personalize the outreach to each group.

Below, we break down the likely reasons for each type of score, the most effective action steps, and the risks for each bucket.

Understanding each situation will help you maximize time, impact, and results of customer success efforts!

4 Quadrants of Customer Usage & Happiness

1. High CSAT, High Usage

**power users who love you**

These are your reference customers and Customer Advisory Board members.

They are the template for sales and marketing to identify the “Ideal Customer Profile.”

More of these please!

The Play:

• Show lots of gratitude and love — holiday gifts, thank you notes, sharing sneak previews, extra access to the team.
• Get them to be case studies (or Customer Win Slides) if they’re not already. Feature your power user and their brand as a way to say thank you.
• Great customer discovery resource for your product team.
• They won’t need you often, but if there’s a support issue or feature request, it’s a good time to give them red carpet treatment.

Risk Assessment:

• Biggest risk = power user change or turnover. Proactively reach out to new users to get them up to speed.
• Second biggest risk = don’t burn them out or take them for granted! :)

2. High CSAT, Low Usage

**Happy under-users**

They use one feature.

They’d be better off with a different tool.

You know they’re at risk but they keep telling you they’re fine!

The Play:

• What’s the *ONE* additional feature that is mostly likely to be helpful? Don’t overwhelm! Their usage is low for a reason — they either don’t have the time or expertise to do more.
• Be VERY proactive. Including helping to build, implement, train, or set up more for them.
• Is there someone else at the company who might be a user? Or use a different part of the app?
• Power user change? Great opportunity to increase adoption!

Risk Assessment:

• Watch out when:
• Budget gets tight
• New boss comes in
• Low-end competitor reaches out to them
• These are at-risk customers but, after an initial effort, unless there’s an internal change, your time is usually better spent elsewhere. It’s hard to fix it when they don’t think it’s broken!

3. Low CSAT, High Usage

**cry for help or too enterprise**

They’re not happy but usage is high.

Usually because they are stretching your tool to the limits.

They need enterprise features like advanced permission settings or multi-tenant management.

Or maybe they’re using your product in a hack-y way (e.g. a B2B tool for B2C company).

Or — best case — this is a cry for help. Remember, angry customers are a good sign!

They care enough to get frustrated and tell you about it.

I’ve seen low scores from:

• an unresolved bug
• a confused first-time user who’s inheriting someone else’s set up
• a feature gap that’s getting resolved soon

The Play:

• Assess why they’re unhappy and if you want to serve this type of customer long term. Good fit? Do everything you can to save them! Bad fit? Help but don’t spend extra time.
• Assuming this is a good-fit customer:
• Understand their key complaints and make an action plan!
• Assign *one* person who is their point of contact if they need extra attention. Don’t bounce them around to different teams.
• New user? Provide extra training and a walk-through of their account.
• Feature or bug issues? Keep them up to date on bugs, support tickets, and/or product roadmap.
• Involve them in feedback sessions or on your customer advisory board.
• Work on creative just-for-now solutions including helping them with manual work arounds.
• The idea is to keep them with you until you can solve their problem. (Or be honest if it’s not the right long term fit!)
• Make sure you understand their North Star metric and see if you can’t generate a Customer Win while you’re working on other items for them.

Risk Assessment:

• Some users will be unhappy but stay with you!
• They can’t afford a different tool.
• You’re the best of bad options.
• They don’t think any tool ever is good.
• If they really suck — unkind to your team, angry, unreasonable, taking up a bunch of time — you should fire them. More on this in a future post!

• Listen carefully. If they’re asking for specific features that a competitor offers, they are looking at other tools. Pull out the stops to save them!

4. Low CSAT, Low Usage

**Very at-risk**

They’re not using and not getting value. Makes sense that their satisfaction is in the dumps.

But they did buy your product initially so someone somewhere thought it would be helpful.

Time to dig in!

The Play:

• The big question is — why is usage so low?
• Over-sold, we can’t do what they want, not a fit
• Small team, no time to implement
• Implementation too complex or technical blocker
• Change in power user immediately after purchase
• Waiting on an internal initiative to get started
• Something else!
• If this customer is a good fit, release the kraken! Kraken being your best customer success strategies:
• a dedicated account manager
• escalating to the “Red Account Team”
• complimentary re-implementation
• engaging sales to help “re-sell” them
• setting up calls with your CEO to really show them the love
• As your Kraken works, make sure you understand your customer’s North Star metric and align to this!

Risk Assessment:

• Is the juice worth the squeeze? It will take a lot of time to increase usage and make this customer happy. Make sure it’s worth it from a revenue and resources perspective.
• Is the customer bought in and willing to put in the time as well? You need a committed internal owner or power user to make it work.

In the wise words of a hilarious, long-time customer success manager:

You can bring a customer to water but you can’t make them drink.

And when they die of dehydration, they’ll blame you!

😂😂😂

Nothing like some snarky customer humor to remind you that — customer success is a two-way street. Even the best Customer Success Manager can’t save an unwilling customer.

Where Do You Start?

In a perfect world, you attack all quadrants at the same time.

But startups do not have unlimited resources (what does, really?) so we must prioritize!

Obviously, use your best judgment based on your unique company, customers, data, and situation.

And there’s a huge caveat to — LOOK AT CUSTOMER CONTRACT AMOUNT!!! This framework assumes that customers are paying about the same or that you’re segmenting first based on customer spend.

So assuming you’re accounting for different customer spend…

Here are some general recommendations to get you started:

• High CSAT/High Usage customers are the most valuable to your business. Least amount of effort, most likely to refer new business or expand, great renewal rate. They won’t take much time but are most important. If you don’t have these, you don’t have a company. Prioritize here!
• All things being equal, Low CSAT/High Usage customers are the most likely to convert to happy customers. They don’t want to leave. And they may have valuable insights or learnings for your team.
• Low CSAT/Low Usage customers MIGHT be worth trying to save. They must be an ideal fit, have willingness on their side, and be paying enough to make it worth it!
• In my experience, High CSAT/Low Usage customers are hardest to influence or shift. It’s a pain point for you but not for them. There’s no incentive on their end to reply to emails, hop on a call, or do more work in the tool.

While your happy, high-usage customers are the priority, it’s realistic to spend 80% of time on unhappy-but-there’s-potential customers, and 20% of time on keeping your best customers happy.

What do you think is more important — customer usage data or self-reported customer satisfaction data?

What strategies are most effective? Any surprising results or effective tactics with different types of customers?

COMING SOON: Which should you start tracking first — usage metrics or customer satisfaction???

Happy (American) Thanksgiving Week!

A great time for me to join the thousands (millions???) of people writing about gratitude.

We’ve shared holiday gift ideas for employees and customers (including free and remote friendly options) before.

Here are fresh, new, hot-from-the-Thanksgiving-oven ideas to show love to your team — whether “team” is employees, family, mentors, friends, or all of the above!

If you’re short on time, money, or both (it’s a startup after all!), here are 5 easy and **FREE** ways to show your appreciation this week — and ANY week!

1. Facilitate A Helpful Intro

For an employee, maybe it’s an intro to mentor or someone in a similar role at another startup. (Also a great way for male leaders to support women!)

For a fellow entrepreneur, a future client.

Investors love intros to founders. (too obvious?? 😜)

Make sure the intro is to someone you personally like and think is awesome!

Bonus points if the intro-ees have a shared interest outside of work.

I never don’t have a good conversation with a fellow running nerd. 🤓

2. Write A LinkedIn Recommendation

No one ever said no to a thoughtful LinkedIn rec!

A sentence or two does the job.

Being proactive (before they ask you) with an employee, customer, or vendor is an incredible move.

Make sure it’s positive without hyperbole. It was SO awkward when I had to remove my glowing review of Sam Bankman-Fried. 😂😂😂

3. Give Public Praise

Even the shyest folks occasionally appreciate a big ole public shout out!

Do it via Slack, a team meeting, or the socials — whatever works with your style and company.

Tie it to a specific project or memorable moment.

Give details on how the person’s strengths or effort impacted the outcome.

The specifics are what make it engaging and special!

4. Craft A Personalized Meme

Nothing says, “I appreciate you” like putting someone’s head on a superhero body.

I’m not even joking!

One of my favorite Rigor moments was when Francis Cordón took a screenshot from a morning check-in and Billy Hoffman turned it into a Slack emoji called the “Kathrynator.”

(A lot of people wear sunglasses to meetings, right?)

THANK YOU, FRANCIS AND BILLY!!! Here is your public shout out!! (See Tip #3)

If you are good at video or use AdPipe, you can up the ante with a fun clip.

Just remember to make it an unequivocally-positive-meme not a possibly-passive-aggressive-snarky-meme!

5. Share Behind-The-Back Compliments

Yes, saying thank you or what you appreciate directly to someone is great.

You know what’s even better?

Sharing something positive that was said about them when they weren’t in the room!

Because there’s no doubt that it was sincere.

And even the most confident folks wonder how they’re perceived.

We made this a “thing” at Rigor when we realized that we rarely gave direct compliments but often sung someone’s praises to others.

We started sharing “behind-the-back” compliments regularly and it was so well received that I continue to do it today.

Certain roles — especially CEOs and founders, but also support reps, engineers, anyone in leadership — hear lots of constructive feedback or grievances without much positive in the mix.

If you hear something good, share it!

What are your favorite simple, no-cost ways to show gratitude???