Reflections on Robinhood’s checking & savings fiasco

We in fintech often confuse Type 1 vs 2 decisions—reversible/not reversible. Robinhood reversed it, yes, but at high cost. As great as tech is, disrupting existing systems first requires wading through minutiae of regs + history.

It’s truly amazing to be part of companies and watch other companies move fast and do incredible things. And perhaps if I were on the Robinhood team I would have come to the same conclusion they did (our hubris will convince us we would “never have done ____________”), but these stories still illustrate to us several key principles:

1. Moving fast is high risk. If you can stomach that risk, great. But be prepared for some decisions to blow up in your face.

2. Ask for counterpoints. Groupthink is deadly. Ask counterpoints from those who agree with you will give you exactly what you expect — not much. Solicit from those who disagree or are willing to disagree.

3. Conduct pre-mortems. While not bullet-proof, when we’ve conducted a pre-mortem (assume your action will fail, and discuss why it did) to poke holes. This helped us identify many of the core issues we would inevitably face. Instead of concluding that “yes, this is awesome” we were able to comprehend, “yes, this is awesome, but _____________” to have a sober, realistic understanding of the land mines that lay ahead of us.

4. Execution is important, but pre-work is even more so. Think of it this way: if you give a presentation on a topic you’ve never spoken about before, where do you spend more time: preparing for your presentation (thinking, slide creation, rehearsing) or the actual presentation?

Sleep on it. I’ve been part of countless decisions where we did “research” (usually about 20 minutes or less). If we only had dug a little bit deeper, we would have realized some glaring issues.

5. Lastly, humility. You are human, you’re far from perfect and you are certainly not invincible. Be the leader who admits they’re wrong, don’t be the leader who is incapable of that.


You check your email. There may be a lot, or there may be a few, but tonight (and it’s Sunday night before a big week) you see one from your boss—or sometimes your boss’ boss. You click on it and see his question. It looks something like this:
Hi [your name],
Please give [name of topic] some thought so we can discuss tomorrow.
And sometimes there is the second piece:
Here are a few thoughts:
  1. We could do it _______
  2. In the meeting, we could focus on ________
  3. [something either wildly different or adding to the existing options]
Sometimes it’s harsher, sometimes it has a specific direction, and sometimes it’s about major obstacles/issues that must be addressed.
You pause. Whatever is physically going on around you at that moment just blurs out. You don’t have an immediate response and so you begin to question yourself. “Do I have what it takes? Can I do this? What if such and such happens?”

We do this to ourselves all the time. We get psyched up. We rev up our fear engine. We go a bit overboard and then our spouse, significant other, friend, or roommate pulls us back to reality. “Man, you’ve got this. You’ve seen this movie before.” And that’s when it dawns on you: your problem isn’t this issue, it’s that you’ve labeled yourself as an imposter and you’re (subconsciously) looking for evidence that you’re a fraud. Instead, when was the last time you got a challenge from a boss, customer, prospect, or project manager and instead told yourself, “I may not have the exact answer at this very moment, but I’ve got a track record of figuring out things that I never knew before. I’m excited and looking forward to this challenge.” Using “track record” and “I’m a problem-solver” aren’t just for your resume, they’re for your every day.
This isn’t some “everybody gets a trophy” BS. Yes, there are people who already think too highly of themselves and they need to come down from the clouds they’re on. And even if they think too highly of themselves, it’s likely because they don’t believe in themselves and crave outside affirmation.
So next time you get that email, phone call, text, or Slack message, stop for a moment and think about it. Even if it is outside of what you believe you’re capable of, use it as a learning experience. The best way forward is to ask questions. Gain insight.
But we get so caught up in the minutiae. There are a million reasons it would fail and the best is that we don’t even try. How many inventions would never have been invented if we, as humanity, simply gave up? I’m sure explorers such as Marco Polo or Captain James Cook had a few more concerns about traveling the unknown world with monsters, demons, and truly foreign lands than we do about our current obstacles. This isn’t self-help affirmation, but an honest question of asking ourselves whether we jump to conclusions too much? What is it that we fear?
If, upon reflection, you decide it’s truly too much, then why and what can you do to get there? What are the steps necessary to accomplish your goal? Break them out. Write them down. Sit down with a friend, spouse, colleague, and family and share your vision and ask for critique.
Because what’s often worse than attempting some major challenge is the idea of sitting alone with our own thoughts. And that, as we know, is filled with anti-affirmations.

Your Team’s Shields Are Down

A couple years ago I read an article called Shields Down describing how people don’t quit the day they resign, they resigned their post a long time ago. It’s when they became vulnerable, when their shields went down that they were open to something new, something different—perhaps where the grass appeared greener.

I was caught juxtaposing that against Customer Success. The concept of Shields Down is true with customers, too. Our customers don’t quit the day they call to cancel, they already decided they were done a long, long time ago.

It’s sometimes really hard to know when someone may be canceling. Heck, they may even be in the product every single day—but that may be just to export all the data. We tend to forget the customer’s story in which:

  1. They weren’t using your product
  2. Found your product/service
  3. Got excited
  4. Dove in—sort of
  5. Got lost, confused, or delayed
  6. Slowed toward ambivalence
  7. Told themselves they would work on it next week, and
  8. Finally decided to cut the cord

Let’s abbreviate that to four steps:

  1. Found your product or service
  2. Got excited
  3. Didn’t engage
  4. Canceled

Why? Because we don’t see where they stopped caring or became apathetic. Think about this: our CRM tell us when we get a new lead, when we’ve determined them as a qualified lead, when we have great conversations to assign a probability of closing, expected close date, sign up date, and onboarding period. But really we lack the apathy-meter. This is for two reasons, 1) there’s much less money in this process than sales and 2) it’s really, really, really difficult to measure this stuff.

The former is changing quickly. So is the second, but to a lesser degree (I invite challenges and arguments. I would love to hear your thoughts!). See, there are health scores. There are ways to quantitatively measure how much a person is using your SaaS product. Heck, that’s often a proxy for delight. Many times these approaches give us a slight early warning system on someone about to pull the ripcord. However, all of those fail because we’re looking at the psychology of people. People make decisions and many times what looks one way for one person will be similar to another. Even if we can get to the point of solving 80-90% of this for our customers there is still one unaddressed piece.

My team.

If I want to keep people on my team, I must think about what to do today to ensure they want to stay here. The decisions teammates make today are not what I may have said earlier this morning or yesterday afternoon, but a cumulation of things from months ago, weeks ago, days ago, and yesterday.

This is cultivation. I love metaphors so let us look through a farmer’s lens.

Like a garden, vineyard, or orchard, we perform actions today not to pick fruit tomorrow, but in an entirely different season. Two years ago I planted two apple trees, two peach trees, and a pomegranate tree. I may get fruit next year. But I expect five full years of growing, nurturing, water, and feeding (compost & fertilizing) before I get a return on my investment. What if I didn’t water a tree today? It would probably survive. At least, for now. But when I forget it for a few weeks (let’s say I was “busy”) I may find it either dead or severely drought-inflicted. There’s a chance I can revive it and bring it back to life, but it’ll still be scared and stunted. I’ll have to be extra careful for the next while to make sure it has plenty of water, and that it hasn’t been afflicted by disease or attacked by vermin or insects. Since it’s especially weak, it’s quite prone to attacks. In effect, shields down.

There are many parallels between cultivating plants and cultivating teammates. But one nice thing about plants and trees is that while they may wilt, they can’t exactly get up and leave. But people can. So whether you’re leading a team or in a team, keep in mind that the actions of today often bear fruit somewhere down the road. Sure, something radical may cause someone to leave today, but people have some level of patience and forgiveness. But after a while, they’ll say “enough is enough.”

Some of our favorite ways of learning about our teammates are through are one-on-ones, performance reviews, and making sure we have an environment that promotes communication, sharing, aligned goals, and a desire and ability to achieve and tackle challenges. No matter what: listen. And not the fake listen, but truly listen—we know when you’re faking it. You’re only fooling yourself.

I hope we can watch our own shields, but also remember to make time to ask about our teammates’ shields. Because otherwise we will be surprised when we get that resignation letter—from the customer or teammate—and neither is fun.




Keeping Customers at All Costs

Anti-discounts, Bad Fit Customers, and Not Doing Whatever It Takes to Retain Them

Awhile ago a few of us Customer Success professionals gathered and discussed the benefits and problems what to do under the following scenarios:
  • Something in the product goes haywire for the customer
  • They’re “going to cancel” because we don’t have such and such feature
  • We don’t have X feature and “they really really want it”
  • We don’t have X feature yet
  • Our competitor has a feature we don’t have, so we need to consider discounting our pricing
Note, the scope was limited to either product failures or missing features.
As you can imagine, this brings about a number of unintended consequences:
  • Devaluing of our product
  • Lost ARR (Annual Recurring Revenue)
  • Enabling the team to kick the metaphorical can down the road
  • Converting customers into missing feature bounty hunters
  • If we’re a pushover here, do we draw the line anywhere?
  • Not being proud of our product
There are certainly more, but, brevity. 🤷‍♂️
You may have not seen a problem with giving temporary or permanent discounts. You may see a problem, but can’t verbalize the implications. You may see the problem, but can’t convince your teammates. That last one is definitely difficult. Focusing on the last one, here are some strategies to help think through the long term implications for your company.
Loss of ARR means less engineering investment
The more discounts you give, the fewer engineers the company can hire. If you do that, you will certainly go into a spiral and will only amplify the need to give more discounts to more dissatisfied customers. That will likely mean fewer or smaller product/feature launches—the exact opposite of what you need.

Gross Margin

Freely handing out discounts also hurts your gross profit margin. If you’re a SaaS company, you need to aim for 80-90% with the higher the better. Giving out discounts lowers your revenue even though you still have to provide services to your customers.
Discounts can be good to help drive your business forward. Unnecessary ones will hurt you.
(Note: you could manipulate your gross margin to be whatever you want. Don’t play accounting tricks.)

Budgeting and forecasting

Similar to above, if you’re constantly giving discounts to many customers, not only does this make your financials look terrible, but this introduces so much ambiguity, uncertainty, and questioning into your forecasting. For instance, how many discounts should we predict for next year? If we do that, how many employees won’t we be able to hire?

“We will build such and such feature by _____”

I think everyone is aware of this, but unless there’s a contractual obligation, committing to a feature or product is a terrible idea. Things change (like roadmaps). Even if that’s the most obvious feature to build, what happens when a major customer asks/demands you to build a different feature? Or industry upheaval or a broad compliance/regulatory change happened? Could you certainly still commit to that timeline?

They’re a bad fit customer / Solving for the wrong problem

If they truly are a bad fit customer, why are you even trying to please them? They’ll always be unhappy because you’re not the product for them. Let them go before they become a major drain on you (mental energy, phone calls, social media complaints, etc.). You wouldn’t keep a toxic friend, why keep a toxic customer?
If you give the discount, you’re solving for the wrong problem and aren’t building a sustainable business. You either have a bad fit customer and need to let them go, or you need to build the product to fit your customers. If you retain bad fit customers, then they will only badmouth your company which will make it harder for sales to win future prospects.

Pareto Principle

Speaking of time, it’s limited. Bad fit customers will tend to require more time from us. So not only do we risk getting badmouthed and hampering marketing and sales, we will also find that we spend 80% of our time on 20% of our customers.

Bounty hunters

If I get one discount because one feature is missing, do I get another discount? What if I find 4 features that are missing? Do I get 4x discounts?

Does the discount hit the company, or the sales rep who sold them?

If I have to give a discount to a customer, can I then dock that sales rep’s commission? If the sales rep is suggesting we give the customer a discount, do they want that permanent discount to come from their future comp?


If you give that discount, it should count as a downgrade and go toward churn. Investors/leadership won’t like that. In fact, no one likes that. If it’s a long term discount (e.g., we likely never will ship that or won’t for X months/years), that’s really a downgrade. We can split hairs here, but it should affect your overall retention figures since the company’s revenue will be less next month than the prior month. 

Roadmap based on discounts

Right now your roadmap is likely based on the likelihood of 1) new sales, 2) retention, and/or 3) account expansion. If we’re doling out discounts for these things, does that mean our roadmap is now designed based on how much money we can get back from shipping the features where we gave discounts? 


Those are just a few reasons. Ultimately, I believe discounts are good for closing deals and a few other areas, but we should think of discounts like salt. Sprinkling some salt on our meal helps enhance the flavor, but too much will ruin it. Discount responsibly.

What is Customer Success Responsible For, Anyway?

I often forget this is a legitimate question, but all I need to do is talk to people entering SaaS and this is completely revolutionary. This approach does not always work in a non-subscription economy. However, in a subscription economy it’s vital. So here goes.

Most everyone understands Customer Success owns Gross Retention. But beyond that, does it own anything else? If so, why? Here are the bare minimum that seem to be agreed on across the spectrum:

  • Onboarding experience
  • Renewals (thus, Gross Retention)
  • Cancellation/retention calls (see above)
  • Some content
    • Partial ownership of the Help Center
    • Perhaps video production
    • Webinars

I think we’re missing a lot here.

Sometimes Customer Success is it’s own division or department, sometimes it’s under Marketing, Sales, or Product…But usually it is its own. It’s not just a subteam. The resources and focus leadership gives to Customers Success is directly correlated to the impact to your bottom line. It’s an investment.


Next, Gross Retention and Net Retention are inexplicably connected at the hip. The happiest of customers are the ones upgrading, adding seats, and sending you referrals. You want to turn customers into fans and fans into raving fans.

Ask yourself who interacts the most with your customers and has the best opportunity to upgrade a happy customer? The focus on the renewal, while necessary, should be the bare minimum. Great Customer Success teams are not only playing defense trying to assist customers. They have direct insights to customer needs and are the number one resource to share upgrades or new products (free or paid). They allow your company to add offense beyond a sales team.


If CSMs are only compensated on the renewal, they won’t help the Sales team or focus on expansion because there’s no incentive. Some will help, and others will try. However, as soon as we inevitably get slammed with tasks, the things we want to do will often fall to the side. Instead, ensure these are included in your CSM job description and comp package.

A CSM’s role is to grow the customer, not keep them stagnant. A CSM should heavily influence:

  1. Renewal (Gross Retention)
  2. Expansion (Net Retention)
  3. Referral (Net Retention? Or as a CS qualified lead?)

So using these three metrics as guiding principles, here’s a better list of what Customer Success should/could own and be responsible for:

  • Onboarding experience
  • Renewals/ongoing relationship (Gross Retention)
  • Cancellation/retention calls (again, Gross Retention)
  • Customer content
  • Voice of the customer
  • Optional: Average Revenue Per User (ARPU)


For one, because we should center our roles around what the customer needs. The customer doesn’t want to talk to one person about renewing, another about expanding, and another about product enhancements. We hate being bounced around with our vendors, why should we treat our customers any different? Let’s own their question and get them their solution—whether a downgrade, upgrade, answer, or creative method of using our software.

Team alignment

Second, because it’s aligning CS with the entire company.


Sales and CS are often at odds with one another. Why? Because their incentives are misaligned. Make them both responsible for account expansion and you may find they want to talk to each other instead of avoiding each other like the plague. Churn already creates enough friction. No need to make it worse. They should be aligned on Net Retention. CS is as responsible for net retention as Sales, if not more.

How often does a customer call their sales rep 2 years later to upgrade? Okay, maybe sometimes. Most of the time they’re going to reach out to Support or their CSM for the upgrade. When their CSM is reaching out to them to check in on their renewal, that’s when they’ll bring up the recently launched features. If there are no Net Retention incentives, why should the CSM bother talking about paid upgrades? It’s more time and energy than it’s worth and the CSM has a million things on their plate, just like everyone else. Align their interests to create collaboration, not conflict.

Marketing and Product

Same is true with Marketing and Product. With new product marketing and product rollouts—CSMs should want to share new features and upgrades. And not just the free ones. If your Marketing and/or Product team(s) are responsible for increasing user engagement in new features, tools, and apps, you better get Customer Success involved. There will be many CSMs who will do it because they care, but if you want 100% adoption across your company now and forever, you’d best align your department’s goals.

Who knows more about your product than the people you hired to help your customers use it? Whether it’s best practices, FAQs, or small tips and tricks, your CS team knows about it. Also, customers like seeing the people they speak with in videos, reading their ideas in blog posts, and talking with them at conferences. Customers build strong relationships with their CS teams and enjoy seeing their success.

Customer Onboarding

Or take the onboarding experience. A trained Onboarding Manager should absolutely focus on the renewal first, but to make that renewal even surer, they need to show them the full ecosystem. First, how many times have we heard, “I wish you had ______ feature” when you already do, but it’s in a higher tier?

Second, Imagine if a CSM for Apple never tried to upsell a customer who only has an iPhone. That customer is more likely to leave than if they have the iPhone, iPad, and Mac. The magic of ecosystems like Apple is that each additional device enhances the experience of all the other devices.

The reason this is important is that the onboarding experience, training calls, content we create, and Knowledge Base should all be optimized for the growth of customers, not just keeping what we have.

No matter the area (content, renewal, training call, QBR), Customer Success Management is at its best when they influence renewals, expansion, and referrals. Otherwise, the company will miss out on terrific reference customers, marketing success stories for prospective customers, and expansion. The focal point for a CS Manager is not retention, but the customer. A proper CS team has the perspective of whatever the customer wants and needs, not just one aspect (renewals).


It’s true that every department should think about the customer’s success and how they can help the customer achieve that. CSMs play a major role in quarterbacking the needs of the customer. Without this explicit ownership, dysfunction easily sets in with all of us touching our noses and saying “not it.”

CSMs are there to be the voice for the customer and be their main connection for the company. Empower them, give them incentives, let them serve the customer and they will serve you and your company. Empower them and they will strengthen your bottom line.