Dec 7 2023

You’ve Seen One, You’ve Seen One

Like all CEOs and VCs, I’m a big believer in the power of pattern matching. I just wrote a whole blog post about the limits of pattern matching after hearing the quote above at a board meeting recently. But then a little alarm rang in the back of my head, and realized that I wrote about the value and limitations of pattern matching here years ago with an even better quote from my father-in-law:

When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra.

So rather that rewrite that entire post, I thought I’d just add onto it a bit here with a current example in my head about executive recruiting and hiring executives. But then I realized I wrote that as well – the myth of the playbook. Think I’ve been blogging too long now, or what?

So let’s focus on these two angles instead: first, how do you know when you’re in a situation where You’ve Seen One, You’ve Seen Them All, or if you’re in a situation where You’ve Seen One, You’ve Seen One? And second, how can you protect yourself from a “seen one, seen one” situation when you are approaching the situation as “seen one, seen them all”?

Here are three ways to think about the decode – is this a pattern or is it a one off?

  1. The list is long. It’s not actually Seen One… so much as it’s Seen X. The longer the list, the more likely you’re seeing a link in a chain instead of a one-off
  2. The item is more everyday/less bespoke. Back to my example in the playbook post I referenced above, hiring a late-stage CFO is bespoke. Hiring an entry level collections person for your AR team is a lot more everyday
  3. The item is more specialized. No two companies are exactly alike. No two SaaS companies are alike, but they’re more alike than two random companies. No two B2B SaaS companies are alike, but they’re even more alike than two SaaS companies. B2B SaaS companies with email marketing platforms. B2B SaaS companies with email marketing platforms serving SMBs. You get the idea

And here are a couple tactics to mitigate against calling a pattern where a pattern doesn’t exist:

  1. Do a premortem (I wrote about this concept in this post) and ask yourself “If this turns out to be wrong, what are the possible reasons it was wrong?”
  2. Build a very small bullet-point level mitigation plan against the top three reasons you come up with

There’s no guarantee that the sound you hear is horses and not zebras. But these indicators may help raise the odds that your pattern match is on point or protect against an unexpected herd of zebras.

Nov 30 2023

Why we use inferior software products

We all interact with dozens of software products every day. Even people who aren’t in tech or don’t have a job that has them staring at a screen all day are constantly using software. I’ve noticed over time that people, myself included, end up using some god-awful pieces of software with terrible design and user experiences and in many cases lesser functionality than competitors.

How can this be?  Isn’t software cheap and ubiquitous at this point?  What’s the excuse for poor UX? Here are four themes I’ve noticed that cause people to use inferior software products.  I am sure there are more.

  • Habit. Some pieces of software start out good or best of breed and get worse over time, either because they don’t incorporate new functionality when competing products do, because competing products have better design or some kind of network effect, or because the product actually has a bad UX team that makes it worse. It’s why I’m still using Apple Music when I should probably be using Spotify
  • Customer lock-in. Some companies make it difficult or undesirable for their customers to switch to a competing piece of software with specific features, housing data, or integrations. Hubspot has done a nice job of gaining share in the CRM space by focusing on companies just starting out. But have they really taken existing installations from Salesforce?
  • Contract terms. Whether price, a long term contract, or that pesky forgotten autorenew clause, frequently you just keep using a piece of inferior software because you’ve already paid for it, or because “that’s what our company standardized on.” Sheets isn’t as powerful as Excel, but it’s free and “good enough”
  • Bundles. It “comes with” is a powerful incentive to use an inferior software product. Broader platforms have an inch-deep but mile-wide approach that captures share from point solutions. Expensify is a much better expense management platform than Ramp, but Ramp does other, more important things (to the buyer in Accounting) well, and they throw in expense management for free

The moral of the story isn’t to use inferior software products. And it’s not to build inferior software products.

It’s that it takes more than a superior product to win over customers. You have a lot more to overcome than just a better feature set or UX.

It’s that your competition could turn out to be someone you didn’t think about who decided to add your whole company as a tab or feature. Keep a much longer list of “maybe, someday” competitors right next to your list of today’s competitors and watch them just as closely.

And it’s that as a disruptive competitor, you need to make it easy for future customers to switch to your platform and migrate their existing data or integrations over. LastPass and 1Password making it so easy to move my data AND even “bought out” my existing subscription.

Nov 16 2023

Should CEOs wade into Politics, Part III (From Tim Porthouse)

I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject.

Your Leadership Game: “No Comment.”

Should you speak up about news events/ politics?

Most of the time, I say, no!

Startup CEOs feel pressure to speak up on news events: Black Lives Matter, Abortion, LBGTQ+ rights, the conflict in Israel/Palestine, Trump vs. Biden. Many tell me they feel pressured to say something, but are deeply conflicted.

Like you, I am deeply distressed by wars, murder, restrictions on human rights, bias, and hate. But if we feel something, should we say something?

Before you speak up, ask the following questions:

1.      Mission relevance. Is your startup’s success or mission on the line? Are customers or employees directly impacted? Example: It makes sense for Airbnb to advocate when a city tries to ban short-term rentals. It makes sense to advocate for your LBGTQ+ employees when a state tries to restrict their rights.

2.      Moving the needle. Will speaking out change anything? If you “denounce” something or “take a stand,” what really happens? Example: If you have employees in a state banning abortion and you tell them your startup will support them as much as the law allows, this could create great peace of mind for employees. But if your startup does not operate in Ukraine or Russia, then denouncing Russia does little (and Russia does not care!)

3.      ExpertiseDo you have a deep understanding of the situation? It’s usually more complicated than it appears, especially at first. Once you speak out, you have painted yourself into a corner you will be forced to defend.

4.      Precedence and equivalenceIf you issue a statement about today’s news event, will you react to tomorrow’s event? Why not? Where do you draw the line?Someone will be offended that you spoke up about X but not Y.

5.      BacklashAre you ready to spend significant time engaging with those who disagree with you?It can get ugly quickly, and mistakes can be costly. Plus, the American public is tiring of business leaders commenting on the news.

6.      Vicarious liabilityWho are you speaking for? When you say, “Our startup denounces X”?Does the whole company denounce it? You don’t know, and probably not. Does the Leadership Team? They may feel pressured to support you. What you are really saying is, “I denounce X!” OK, great, then say it to your friends and family. Leave your startup to talk about business.

If your answers are “yes,” – then speak out.

If not, I recommend keeping quiet.

In my opinion, our job is to build great companies, not debate current events.

By not speaking out, you can say, “We don’t talk politics here.” You can shut down any two-sided arguments at work and say, “Let’s get back to work,”removing a big distraction. Remember when employees protested because Google was bidding for Pentagon contracts?

I realize that you will be challenged to make a statement, that, “Saying nothing is unacceptable/ complicit.” But whoever challenges you will only be satisfied if you support their view.

If you still want to speak out, I respect your choice. Some of you will be angry with me for writing this, and I accept that. I’m asking you to think carefully before you make a statement.

Nov 9 2023

Everything vs. Anything

I heard two great lines recently applied to CEOs that are thought provoking when you look at them together:

You have to care about everything more than anything


You can do anything you want but not everything you want

Being a CEO means you are accountable for everything that happens in your organization. That’s why you have to care about everything. People. Product. Customers. Cash flow. Hiring. Firing. Board. Fundraising. Marketing. Sales. Etc. You can never afford not to care about something in your business, and even if there’s a particular item you’re more focused on at a given point in time, you can never get to a place where you care about any one particular thing more than the overall health of the business.

But caring is different than doing. As a CEO, even if you’re hyper productive, you can’t do everything you want to do – and you shouldn’t. Others in your organization have to take ownership of things. And you can’t burn yourself out or spread yourself too thin. But you do have the prerogative of doing anything you want in and around your company as long as you do it the right way.

This second line is particularly interesting when applied to a CEO’s activities outside of work. As with anyone, it’s critical for CEOs and founders to have outside hobbies and interests, time for friends and family, down time, and even non-work work time like sitting on outside boards. Staying fresh and “sharpening the saw” is good for everyone. A CEO should be able to do anything she wants outside of work — from sitting on outside boards to being in a band. But a CEO can’t do everything she wants outside of work while still devoting enough time and attention to work.

Taken together, the two lines are interesting. As a CEO, you have to care about everything, but you can’t do everything. That pretty much sums up the job!

Nov 2 2023

Measure Twice, Cut Once

The old carpenter’s axiom of being extra careful to plan before executing is something not enough executives take to heart in business. Just like cutting a piece of wood a little too long, sometimes you execute in ways that can be modified on the fly; but other times, just like the cases where you cut a piece of wood too short, you can’t. And of course, in business, sometimes it’s somewhere in between. Some examples:

  • One example that’s a little more literal is around cutting staff or planning a layoff. Layoffs are traumatic for everyone involved – mostly those impacted, but for you as CEO and for your remaining organization as well. Being thoughtful about how much you cut and (unlike the case of a piece of wood) erring on the side of cutting more than you think you need to can prevent you from having to do a second set of even more traumatic layoffs down the road
  • Getting a lease on a new office? Plan, plan, and plan again – you can end up spending too much if you get too much space and can’t sublet it…you have a real headache if you don’t get enough space and need to scramble for more
  • Planning a major investment in a new product? You don’t want to spin up a whole new effort internally and hire people before you’ve done enough discovery and planning to know it’s worth it

It’s an interesting question as to whether or not this axiom conflicts with the startup mentality of moving quickly and with agility. I don’t think it does, although in the startup ecosystem, a lot of fixed decisioning has moved to variable, which means you may be faced with fewer times where you need to measure twice. For example, a lot of SaaS licenses you have to buy are per-seat, or AWS costs are fluid. All that is much easier than perpetual license software models or standing up servers in a data center.

I’m a big fan of Eisenhower’s line that “plans are nothing but planning is everything.” That’s why I like to measure twice, cut once when I’m working on something big. It just raises the odds of getting it right, whatever it is.

Oct 26 2023

When All You’re Holding is a Hammer, Everything Looks Like a Nail

One of the things I love about the business we’re building at Bolster is that we’re creating a whole new way for companies to access executive talent. It’s not just that we do full-time searches better, faster, and cheaper than traditional search firms. It’s that we approach the whole topic differently and with a more flexible mindset that matches the dynamic needs of our startup and growth stage clients.

As I wrote last week in You Don’t Need a CRO, CEOs often come to us thinking they need a full-time executive – usually a CRO or COO. And sometimes they do. If we were an executive search firm, we might agree and sell them the thing that we have to sell, which is full-time searches.

But a full-time senior executive is often the wrong answer to whatever problem the CEO is feeling at the moment. Sometimes it’s that they’re just overwhelmed and need help. Sometimes someone on their team isn’t scaling. There are a lot of other options out there for getting executive-level help, advice, and deliverables without making a full-time hire, for example:

  • Fractional executives who can work as much as half time and as little as a day or two per month, giving you many of the benefits of an experienced executive without all of the cost and risk and equity commitment
  • Project-based executives who can come in and help you with a specific thing you don’t know how to do or don’t have time to do yourself
  • Functional mentors to help level up someone on your team with expertise you may not have yourself
  • Independent directors to help add whatever voice is missing from your leadership team, whether it’s the voice of the customer or an experienced operator in a given function or domain

In the world of startups and growth companies, staffing at the most senior and expensive levels needs to be nuanced. That’s why I’m glad we have a lot of different options to help CEOs out. Because if all we were holding was a hammer, everything would look like a nail.

Oct 19 2023

You Don’t Need a CRO

One of the most common things early stage CEOs say to me once they find product-market fit and make a few sales is “I need a CRO.” The answer is almost always, “no, you don’t.” A couple years ago I wrote about the evolution of enterprise selling organizations in this post. Reading that is a good place to start this topic. Go ahead…I’ll still be here when you come back.

Welcome back!

So in the early days of a company, it’s all “selling on whiteboard.” The need that early stage CEOs have that prompts them to tell me they need a CRO is simple the need to have help selling.

What the CEO really needs is a couple of very good early stage sales reps. People who are senior enough and clever enough to hold clients’ attention. People who are junior enough to accompany the CEO or other founders on dozens of “selling on whiteboard” sessions with clients to be able to start doing that work on their own. And People who can help the transition from “selling on whiteboard” to “selling on Powerpoint” by doing some very basic documentation of the selling process, buying centers, influencers, and value proposition.

It may also be true that the CEO doesn’t really know much about sales — maybe it’s a technical founder, or even a founder who came up through marketing or product management — and that part of the “I need a CRO” comment is really just an admission that the CEO doesn’t really know how to structure and manage a sales effort. In that case, my first suggestion is that the CEO read the excellent Startup Sales section within Startup CXO. And if that’s not enough, then there are over 1,200 fractional CROs in the Bolster marketplace who can give you anything from an hour of consulting to a couple days per week as a fractional executive to help you put some structure in place for your new sales reps. Once you have a repeatable sales motion, you can hire more reps and a Sales Manager/Director or VP.

So no, you don’t need a CRO. But there are lots of things you can do to get the help you need in the early days of selling that are less expensive, less risky, and a better fit for early stage companies.

Oct 12 2023

Chief People Officer Pitfall for Later Stage CEOs

(This is a bonus quick 5th post, inspired by long time reader Daniel Clough, to the series that ended last week about Scaling CPO’s- the other posts are: When to Hire your First Chief People Officer, What does Great Look like in a Chief Privacy Officer, Signs your Chief Privacy Officer isn’t Scaling, and How I Engage With The Chief People Officer.)

As I’ve noted over the years, the Chief People Officer role is a tough one to get right and a tough one to scale with the organization if what you’re really looking for is a strategic business partner who can lead not just the important blocking and tackling in HR but innovates the people part of your organization, building new systems and programs, approaches recruiting as building great teams instead of filling seats, helps manage your company operating system, and developing and coaching leaders.

A number of later stage CEOs I mentor have come to me over the years when they have a sub-par Chief People Officer and said something like “I’m going to put HR under my CFO.” To me, that’s a bit of a cop-out – it’s acknowledging that the person in the role isn’t strong enough to be a full-throated executive, but the CEO doesn’t want to go through the hassle or expense of replacing them.

Here’s my answer when I hear that from a CEO: “Ok, then your CFO will actually now become your Chief People Officer.  You must have a Chief People Officer on the exec team reporting to you.”

There are few things about which I have a stronger point of view. Someone in your organization must have strategic oversight for human capital. If it’s not your head of HR and you can’t bear recruiting/replacing that person, then it needs to be whoever your put that person under. Or it’s you. But at even mid-scale companies, why would you take that responsibility on yourself?

Oct 5 2023

Scaling Tip: Spend Less Time Talking. And Spend More Time Talking

One of my top 10 scaling tips for CEOs as they take a business from startup to scaleup keys in on communication patterns. As your company grows from 0-25 employees to a place where you no longer work hands-on with most of the team, which is really >25 but gets more and more true at every step beyond that, you need to rethink how you handle employee conversations in many ways. My tip sounds confusing, but let me break it down.

Spend less time talking. The less you know about the day to day details of everyone’s job and experience, the more time you need to spend learning and keeping in touch with those details from others. The only way to do that is by asking questions, listening to responses and watching body language, and then asking follow-up questions. As I mentioned here in Inquiry vs. Advocacy, you know what you have to say…what you don’t know is what the other person has to say! The more you listen and learn as your company scales, the more effective you can be at steering the ship.

And yet…Spend more time talking. This isn’t as contradictory as it sounds. What I mean by this is that the further away you are from the front lines and the smaller the percentage of the team who really know you and have casual interactions with you, the more time you need to spend repeating key messages – things like what the goal is, critical metrics and progress, how each team and person’s work rolls up to the big picture. I always appreciate the “rule of three” around things like this, which is simply that people need to hear the same message three times before they start to internalize it. What that means for you is that just as soon as you get tired of saying the same thing over and over in various groups internally…it’s finally starting to hit home, and you need to keep doing more of the same.

How and when you communicate with the company may also change – the mix and frequency of 1:1 meetings, small group meeting, large group meetings, and email/written communications will need to evolve. But that evolution of the “what” is secondary to the above principles of the “how.”

Sep 28 2023

How I Engage With The Chief People Officer

Post 4 of 4 in the series of Scaling CPO’s- the other posts are, When to Hire your First Chief People Officer, What does Great Look like in a Chief Privacy Officer and Signs your Chief Privacy Officer isn’t Scaling.

You won’t have a ton of time to engage with the Chief People Officer but there are a few ways where I’ve typically spent the most time, or gotten the most value out or my interactions with them. So, you’ll need to capitalize during those few moments when you do get a chance to engage with the Chief People Officer.

I ALWAYS work with the CPO as a direct report.  No matter who my HR leader is, no matter how big my executive team is, no matter how junior that person is compared to the other executives. I will always have that person report directly to me and be part of the senior most operating group in the company.  That sends the signal to everybody in the company that the People function (and quite frankly, diversity, culture, and a whole host of other things) are just as important to me as sales or product. I guess that’s walking the walk, not just talking. If I’m not serious about diversity, about our core values, and about the people in the company, no one else will be either. So, I always have the CPO as a direct report.

A second way to engage with the CPO is to insist on hearing about ALL people issues. First, I am a very “retail-oriented” CEO, and I like to engage with people in the business—at all levels, in all departments, and in all locations.  So I like know what’s going on with people — who is doing particularly well and about to be promoted, who is struggling, who is a flight risk, who is going through some personal issue (good or bad) that we should know about. This isn’t prying into people’s lives, but a real way to engage with people beyond business and a way to show that you care about them as a person. Even more than just me wanting to be in the know, I want others in the company to have a deep level of awareness of our contributors. For example, in our Weekly Sales Forecast meeting at Return Path, because our head of People knew that I wanted to know about all these details on our employees, they insisted that all the other People Business Partners roll those issues up as well. That means everybody in the room was in the know as well.  It’s not just to have a better understanding of people, there’s a business case for knowing what’s going on at a very detailed level and the number of issues we nipped in the bud, the number of opportunities we were able to jump on to help employees over the years because of this retail focus, has been immense.

I also engage with the CPO as an informal coach for myself and with my external coach.  In an earlier post I mentioned that a great Chief People Officer can—and should—call a CEO out when a CEO needs to be called out.  And that also means that great Chief People Officers engage with CEOs deeply about how they are doing, they help CEOs process difficult situations, and help them see things they might not otherwise see.  Being a CEO is a lonely job sometimes, and it’s good to have a People partner to be able to collaborate with on some of the most personal and sensitive issues.

Finally, I engage with the CPO to design and execute Leadership/Management training.  This is an important skill that a great CPO brings to the company and I have found that it is the best way to create a multiplier effect of employee engagement and productivity. The CPO in your organization needs to teach all leaders and managers how to be excellent at those crafts — and how to do them in ways that are consistent with your company’s values.  This is a tall order for one person to put together so I always took a lot of time, in large blocks of hours or days, to either co-create leadership training materials and workshops with my head of People, or to lead sessions at those workshops and engage with the company’s managers and leaders in a very personal way.  That always felt to me like a very high ROI use of time.

(You can find this post on the Bolster Blog here)

Sep 21 2023

Why Have a COO?

The following is a guest post written by my dad, Bob Blumberg, long-time tech entrepreneur and now startup advisor and board member (yes, the apple doesn’t fall far from the tree).

To create a successful and sustainable, growing and profitable business, the leadership of the company must have both strategic and tactical understanding and capability.

For this purpose let us define “strategic” as having the understanding of the customer, his problem, need, or desire, a knowledge of his own industry, its past, present, and likely future, how developments in other industries can be applied to his own, and how to envision the product or service that will succeed.

In contrast, “tactical” is the understanding of how to get things done, how to accomplish the strategic goals.  It is composed of the knowledge of how to organize and structure, who and how many to hire or assign, how to market and sell, how to best the competition, how to produce and sell it profitably.

More often than not, these two mind- and skill- sets do not reside in the same person.  If that is true, it is critical that the CEO recognize it, and hire or promote a COO with the complement to his own ability.  If the CEO is strategic, his tactical counterpart could be COO or a VP of Sales, Manufacturing, Finance or HR, that he is willing to listen to.  Similarly, if the CEO is tactical, his strategic counterpart should be COO or a VP of Marketing, Engineering , or Product Marketing/Management.

In either case, the strategic leader should have deep background and significant experience in the industry, in competitors, his own company, or both over the course of his career.  The tactical leader can be more of a professional manager, with a broader range of experience, able to bring knowledge of different ways of getting things done.

Obviously, mutual respect between the two is essential.  Industry probably has many examples of this.  One that comes to mind is Facebook, where Mark Zuckerberg as a strategic CEO relied heavily on Sheryl Sandberg as his COO.  Although it is certainly possible to find both qualities in a CEO, it may be rare, and the successful CEO will realize where his talents are and are not, and hire or promote accordingly.

When my dad sent this to me, I responded with the following: Here’s a follow up question that I’d like to include in the post – at what size company do you think this kicks in? In Startup CXO, I wrote that for really early startups of 10-15 people, when a CEO says they need a COO, it can be a crutch because they just don’t know how or don’t care to do basic management work, what you’d define as tactical work. It’s often not fun for creative entrepreneurs. But maybe that’s not right, maybe it’s just the case that some people aren’t cut out to do that kind of work, and that’s ok. Dad’s response:

I think someone has to be looking at both from the start.  The complement to the CEO doesn’t have to have the title of COO, but needs to be on the team in some senior position, and have the respect of the CEO for his/her complementary skillset.