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

and

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!

The Problem with Titles

This will no doubt be a controversial post, and it’s more of a rant than I usually write. I’ll also admit up front that I always try to present solutions alongside problems…but this is one problem that doesn’t have an obvious and practical solution.  I hate titles. My old boss from years ago at MovieFone used to say that nothing good could come from either Titles or Org Charts – both were “the gift that keeps on giving…and not in a good way.”

I hate titles because they are impossible to get right and frequently cause trouble inside a company. Here are some of the typical problems caused by titles:

• External-facing people may benefit from a Big Title when dealing with clients or the outside world in general. I was struck at MovieFone that people at Hollywood studios had titles like Chairman of Marketing (really?), but that creates inequity inside a company or rampant title inflation
• Different managers and different departments, and quite frankly, different professions, can have different standards and scales for titles that are hard to reconcile.  Is a Controller a VP or a Senior Director?  And does it really matter?
• Some employees care about titles more than others and either ask or demand title changes that others don’t care about.  Titles are easy (free) to give, so organizations frequently hand out big titles that create internal strife or envy or lead to title inflation
• Titles don’t always align with comp, especially across departments. Would you rather be a director making $X, or a senior manager making $X+10?
• Merger integrations often focus on titles as a way of placating people or sending a signal to “the other side” — but the title lasts forever, where the need that a big title is fulfilling is more likely short term
• Internal equity of titles but an external mismatch can cause a lot of heartache both in hiring and in noting who is in a management role
• Promotions as a concept associated with titles are challenging.  Promotions should be about responsibility, ownership and commensurate compensation.  Titles are inappropriately used as a promotion indicator because it inherently makes other people feel like they have been demoted when keeping the same title
• Why do heads of finance carry a C-level title but heads of sales usually carry an EVP or SVP title, with usually more people and at least equal responsibility?  And does it sound silly when everyone senior has a C level title?  What about C-levels who don’t report to the CEO or aren’t even on the executive team?
• Ever try to recalibrate titles, or move even a single title, downward?  Good luck

What good comes from titles?  People who have external-facing roles can get a boost from a big title. Titles may be helpful to people when they go look for a new job, and while you can argue that it’s not your organization’s job to help your people find their next job, you also have to acknowledge that your company isn’t the only company in the world.

Titles are also about role clarity and who does what and what you can expect from someone in a department.  You can do that with a job description and certainly within an organization, it is easy to learn these things through course of business after you join.  But especially when an organization gets big, it can serve more of a purpose.  I suppose titles also signal how senior a person is in an organization, as do org charts, but those feel more like useful tools for new employees to understand a company’s structure or roles than something that all employees need every day.

Could the world function without titles?  Or could a single organization do well without titles, in a world where everyone else has titles? There are some companies that don’t have titles. One, Morning Star, was profiled in a Harvard Business Review article, and I’ve spoken to the people there a bit. They acknowledge that lack of titles makes it a little hard to hire in from the outside, but that they train the recruiters they work with how to do without titles – noting that comp ranges for new positions, as well as really solid job descriptions, help.

All thoughts are welcome on this topic.  I’m not sure there’s a good answer.  And for Return Pathers reading this, it’s just a think piece, not a trial balloon or proposal, and it wasn’t prompted by any single act or person, just an accumulation of thoughts over the years.

There’s been a growing cry for tech companies to add diversity to their leadership teams and boards, and for good reason. Those two groups are the most influential decision making bodies inside companies, and it’s been well documented that diverse teams, however you define diversity — diversity of demographics, thoughts, professional experience, lived experience — make better decisions. 

Gender, racial, and ethnic representation in executive teams and in board rooms are not new topics.  There’s been a steady drumbeat of them over the last decade, punctuated by some big newsworthy moments like the revelations about Harvey Weinstein and the tragic murder of George Floyd.  

It’s also true that in people-focused organizations, and most tech companies claim to be just that, it’s beneficial to have different types of leaders in terms of role modeling and visibility across the company. As one younger woman on my team years ago said, “if you can see it…you can be it!”

My company Bolster is a platform for CEOs to efficiently build out their executive teams and boards. But while nearly every search starts with a diversity requirement, many don’t end that way. 

Here’s why, and here’s what can be done about it. 

For boards, the “why” is straightforward. Board searches are almost never a priority for CEOs. They’re viewed as optional. Bolster’s Board Benchmark study in 2021 indicated that only a third of private companies have independent directors at all;even later stage private companies only have independent directors two-thirds of the time. That same study indicated that 80% of companies had open Board seats. The comparable longitudinal study in 2022 indicated that the overwhelming majority of those open board seats were still open. 

Independent directors are usually the key to diversity, as the overwhelming majority of founders and VCs are still white and male. It takes a lot of time and effort to recruit and hire and onboard new directors, and in the world of important versus urgent, it will always be merely important. Without prioritizing hiring independents, board diversity may be a lofty goal, but it’s also an empty promise. I wrote about my Rule of 1s here and in Startup Boards – I wish more CEOs and VCs took the practice of independent boards and board diversity seriously. The silver lining here is that when CEOs do end up prioritizing a search for an independent director, they are increasingly open to diverse directors, even if those people have less experience than they might want. That openness to directors who may never have been on a corporate board (but who are board-ready), who may be a CXO instead of a CEO, is key. Of the several dozen independent directors Bolster has helped match to companies in the past year, almost 70% of them are from demographic populations that are historically underrepresented in the boardroom.

Diversity is stalling for Senior Executive hiring for the opposite reason. Exec hires are usually urgent enough that CEOs prioritize them. And they frequently start their searches by talking about the importance of diversity. But Senior Executives are much more often hired for their resume than for competency or potential. Almost all executive searches start with some variation of this line, which I’m lifting directly from a prior post: “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to be hired. They have made a ton of money, and they have moved beyond that job in their career progression. So inevitably, the search moves on to look for the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people may or may not be easy to find or available, but they feel less risky. In the somewhat insular world of tech, those candidates are also far less likely to be diverse in background, experience, thought, or, yes, demographics.

Running a comprehensive executive search based on competencies, cultural fit, scale experience, and general industry or analogous industry experience is much harder. It takes time, patience, digging deeper to surface overlooked candidates or to check references, and probably a little more risk taking on the part of CEOs. And while CEOs may be willing to take some risk on a first-time independent director, fewer are willing to take a comparable level of risk on an unproven or less known executive hire. 

For some CEOs, the answer is just to take more risk — or more to the point, recognize that any senior hire carries risk along a number of dimensions, so there’s no reason to prioritize your narrow view of resume pedigree over any critical vector. For others, the answer may be to bring the focus of diversity in senior hires to “second level” leaders like Managers, Directors, or VPs, where the perceived risk is lower, and the willingness to invest in training and mentorship is higher. Those people in turn can be promoted over time into more senior positions. 

Not every executive or board hire has to be demographically diverse. Not every executive team or board has to have individual quotas for different identity groups, and diversity has many flavors to it. But without doing the work, tech CEOs will continue to bemoan the lack of diversity in their leadership ranks, and miss out on the benefits of diverse leadership, while not taking ownership for those efforts stalling.

(This post was written by my colleague Bethany Crystal and originally published on the Bolster blog yesterday. While I am still trying to figure out what posts to put on this blog vs. Bolster’s blog since the blogs are pretty similar, I will occasionally run something in both places.)

At Bolster, we believe that 2021 will mark the rise of the on-demand economy for executives. More than ever before, executives are seeking out roles that distinctly aren’t full-time for a variety of reasons – they’re in between full-time roles and want to stay engaged and meet a wide range of potential employers; they’re retired or semi-retired/post-exit and want to keep working, just not full-time; they’re fully employed but are looking for advisory opportunities to help others; or they are committed to the more flexible lifestyle that being an on-demand affords. As business leaders, you might be wondering how to take advantage of this trend and incorporate on-demand talent onto your existing team. Don’t worry – we’ve got you covered.

Let’s start with a quick primer on the distinct types of on-demand talent. Here are the four most common themes we see among our member network at Bolster:

The Four Types of On-Demand Talent

1. Interim: Someone who is partially or fully dedicated to working with your company, but only temporarily (you can think of them as “filling a gap”)
2. Fractional: Someone who works part-time (or “fractionally”) with your company on an ongoing basis (they “own” the function on a long-term, part-time basis)
3. Advisor or Coach: Someone who supports your existing team by offering external advising, coaching, or mentorship as needed (this might be on a temporary or long-term basis)
4. Project-Based: Someone who is brought on to complete a specific project or a fixed span of work (this is the closest to typical consulting work)

Depending on your business needs, the capacity of your existing team, and your resourcing, you might find it useful to have one or more on-demand executives in the mix at any given time. We’ve also found this can be a great way to keep things fresh at the leadership level and make sure new ideas are circulated with some regularity.

Business Opportunities for On-Demand Talent

While every company’s on-demand talent needs will vary, we’ve already seen a few patterns emerge from the 2,000 executives in our member network. Here are a few times to think about bringing on-demand work to your business.

Choose interim work if you need…

• A temporarily placeholder at the exec level
  Whether unexpected or planned, transitions at the executive level can come with a high cost: Any week that goes by with an unfilled seat adds more work to the team, contributes to business lag, or both. While full executive searches can take six months (or more!) to get right, many CEOs find it helpful to bring on interim help as a “stopgap” in the meantime. The most obvious benefit of interim on-demand work is to prevent your business from falling behind in areas where you may not have a deep bench below the executive level. And you might also consider that bringing in a seasoned professional as you conduct your full-time search will give your team a proxy to compare against, making that placement process a bit easier. Last – while it’s not a guarantee, there’s always the chance that your interim hire is a great fit for you and wants to stick around for the long term! You then benefit from an on-the-job “interview” or audition.
• Surge capacity staffing
  Imagine a situation where your business doesn’t need an executive in a particular function. You’re small, scrappy, and you’re getting along perfectly well with the team you have in place – and you can fill in the bits of executive leadership required for that function yourself from time to time. But then something pops up where you need to be the CEO and can’t afford to ALSO be the CXO. An interim CXO could be the right solution. For example, the 3-5 months run-up to a Series A or B financing could be a good time to bring on an experienced CFO if your only relevant team members are handling AP, AR, and Payroll. Or you could be working on your company’s public launch with a less experienced marketing team and an agency – and an interim CMO could make all the difference between success and sideways.
• Parental leave coverage
  With a growing business trend of increased parental leave coverage, CEOs are starting to use interim executives to fill holes that might temporarily exist on the leadership team. Interim work is particularly useful if there isn’t an obvious “second in command” role on that team who might take on a stretch project in their absence. Implemented correctly, bringing on an interim exec can also help to squash any fears of “getting replaced” while someone is away on leave. As an added bonus, bringing in a new face (if only temporarily) can give the remaining team a chance to “try out” a new leadership style and share feedback about what worked and didn’t work during the interim period.

Choose fractional work if you need…

• A seasoned professional’s experience and skillset (but not all the time)
  Before every full-time leadership hire, there is the sticky “in between” period of need. That’s the period when some work starts piling up, but not quite enough to fill an entire work week for one person at the executive level – or the period when you know you need a more seasoned leader in a function but just can’t afford one full-time. If you don’t have an experienced executive in the role, you miss opportunities for effectively setting up scalable practices and processes. Often, a lack of senior focus in a functional area means that you miss strategic opportunities, and sometimes it also means that you expose yourself to risk that could be avoided with the right person having ownership of the function. This is the perfect time to introduce fractional work to your business. The most classic example of fractional executive talent is the CFO who oversees the bookkeeping and accounting for several companies at once. But you can find a fractional executive for just about anything. You might consider this type of on-demand executive if you don’t yet have anyone in that functional area, if you have a team of less experienced specialists or even a more junior generalist leader in that functional area, if you want a taste of what it’d be like to dedicate more resources there, or if you need just a few things done right, without having to think about them yourself.

Choose advisory or coaching work if you need…

• Mentorship for your current executives
  Sometimes it’s helpful to see what “great” looks like in order to achieve greatness yourself. If you’re looking for a way to give a current leader an added boost to their development plan, consider bringing on someone who can serve as a mentor or advisor on a temporary or long-term basis. Someone who has been in your shoes before and can give advice and guidance based on their experience. This on-demand exec role has two big benefits: The first being that it demonstrates to your executive team that you’re committed to their ongoing success and growth, which boosts morale (and hopefully performance). The second is that you’ll be able to equip your current team with the tools they each need to scale instead of having to bring on a new wave of executives for each business stage. The advisor or coach usually works a few hours per month, once they’ve set up a strong coaching relationship.
• Access to top talent without the full-time price tag
  Just as remote work unlocked the potential to find “the best of the best” without geographic constraints, on-demand work does the same at the executive level. More and more, we’re seeing CEOs incorporate advisors to their business as a way to gain exposure to best in class talent (at a fraction of the cost). This can be a great way to introduce subject matter or functional expertise into your organization without committing to a full-time salary.

Choose project work if you need…

• A fixed-scope expert engagement at the executive level
  Just as tools like Task Rabbit made it possible to find experts to accomplish tasks on a personal level (such as moving furniture or painting a bedroom), on-demand talent makes it possible to find seasoned executives to complete one-off projects at an expert level. That’s why, on Bolster, we ask each each member to indicate what roles they can take on, and also what projects they can be hired to do. As a CEO, you might consider outsourcing some of the crunchy stuff at the exec level that might take a lot of time, or in cases where you need a quick turnaround to get to an MVP. Common projects we’ve seen to date include building sales commission plan structures, designing a go-to-market launch plan for a new product, running due diligence on an acquisition, overhauling pricing and packaging, working on a strategic plan, TAM analysis, budgeting process, or creating a diversity & inclusion strategy for the company.
• An experimental project that won’t distract the current team
  One final area where you might consider on-demand work is for a project that feels more like an addendum to your current business, or an early experiment. At Bolster, we brought on an on-demand executive to help us think through and roll out a brand new product that we’re in the early days of testing right now. We’ve seen other CEOs use project-based work at the exec level for things like evaluating market expansion possibilities or speccing out the MVP of a potential new product.

This is just a short list of some of the possibilities where on-demand talent might support you in your business today. One of our favorite parts about this type of work is just that – the flexibility it offers to you and your team. Whether your business is just getting started or if you’re operating on all cylinders, don’t forget to consider on-demand work as part of your CEO toolkit for this year and beyond.

– Bethany Crystal, February 2, 2021

I was trading emails a few weeks ago Elliot Noss from Tucows about the current state of the economy after being on a panel together about it, and he wrote:

The market is fascinating right now. Heated competition AND layoffs and hiring freezes. It feel like an old European hotel where there are two faucets, one is too hot and the other too cold.

While a quick rant about European hotel bathrooms could be fun…we’ll just stick to the sink analogy. As anyone who has ever tried to use one of these sinks that Elliot describes knows, they’re hard to use and illogical. Sure, sometimes you want freezing water and sometimes you want scalding water (I guess), but often, you want something in between. And the only way to achieve that is to turn on both freezing and scalding at the same time? That’s weird.

Then I was on another email thread recently with a group of CEOs, when John Henry from Ride With Loop said this:

Whatever the climate, we all surely agree there is no bad time to build a good business.

How true that is!

But here’s the worrisome part. It’s impossible to predict what’s going to happen next. We are in uncharted territory here with a land war in Europe, a partial global oil embargo of a top tier oil producer, a pandemic, supply chain problems, etc. etc. There are days and circumstances where everything feels normal. Plenty of businesses, especially in the tech sector, are kicking ass. And yet there are days and circumstances that feel like 2001 or 2009. It’s tough to navigate as a startup CEO. Yes, it’s obvious you should try to have a couple years of cash on hand, and that you should be smart about investments and not get too far ahead of revenue if you’re in certain sectors (presumably if you’re in an R&D intensive field and weren’t planning to have revenue for years on end, life isn’t all that different?). But beyond that, there’s no clear playbook.

And that’s where the worrisome line comes in. I saw Larry Summers on Meet the Press last weekend, who predicted that

a recession would come in late 2023.

Wait, what? Aren’t things messed up now? Yes, inflation is high, the stock market is down, and interest rates are creeping up. But the economy is still GROWING. Unemployment is still LOW. Summers’ point is a reminder that contraction is likely, but it may still be a ways off, it depends how the Fed handles interest rate hikes (and about a zillion other things), and it’s impossible to predict. That was more worrisome to me. If we’re navigating choppy waters now, it may not just be for a couple of quarters. It may be that 4-6 quarters from now, we are in for 2-3 quarters of contraction. That is a more than most companies are able to plan for from a cash perspective.

Frothy macro environments lead to bad businesses getting created, too many lookalike businesses popping up, or weak teams getting funded. When the tide goes out, as they say, you can see who is swimming naked. But if you’re building a good business, one that has staying power and a clear value proposition, with real people or clients paying real money for a real product or service, and if you’re serious about building a good company, keep on keeping on. Be smart about key decisions, especially investment decisions, but don’t despair or give up.

We’ll all get through this.

It’s Copyright Time

Brad must be off his game this year, so…time to update all those copyrights to say 2008.  Or as Brad gently suggested last year, make that field variable so you never have to worry about it again!  (Thanks to our CTO Andy Sautins for the reminder here.)

Please, Keep Not Calling (Thank You!)

It’s been three years since the federal government passed one of its better pieces of legislation in recent memory, creating the Do Not Call Registry which is a free way of dramatically reducing junk phone solicitations.  At the time, registrations were set to expire every three years.  When I signed up my phone number, I stuck a note in my calendar for today (three years later) to renew my registration.  I was planning on blogging about it to remind the rest of the world, too.

To my great surprise, when I went to the site today, I saw this note:

Your registration will not expire. Telephone numbers placed on the National Do Not Call Registry will remain on it permanently due to the Do-Not-Call Improvement Act of 2007, which became law in February 2008.

That’s two great pieces of legislation.  What will they think of next?

Return Path Core Values, Part II

As I said at the beginning of this series, I was excited to share the values that have made us successful with the world and to also articulate more for the company some of the thinking behind the statements.

You can click on the tag for all the posts on the 13 Return Path’s core values, but the full list of the values is below, with links to each individual post, for reference:

1. We believe that people come first
2. We believe in doing the right thing
3. We solve problems together and always present problems with potential solutions or paths to solutions
4. We believe in keeping the commitments we make, and communicate obsessively when we can’t
5. We don’t want you to be embarrassed if you make a mistake; communicate about it and learn from it
6. We believe in being transparent and direct
7. We challenge complacency, mediocrity, and decisions that don’t make sense
8. We believe that results and effort are both critical components of execution
9. We are serious and passionate about our job and positive and light-hearted about our day
10. We are obsessively kind to and respectful of each other
11. We realize that people work to live, not live to work
12. We are all owners in the business and think of our employment at the company as a two-way street
13. We believe inboxes should only contain messages that are relevant, trusted, and safe

As I noted in my initial post, every employee as of August 2008 was involved in the drafting of these statements.  That’s a long post for another time, but it’s an important part of the equation here.  These were not top-down statements written by me or other executives or by our People team.  Some are more aspirational than others, but they are the aspirations of the company, not of management!

We were excited to close the sale of our Consumer Insights business last week to Edison, as I blogged about last week on the Return Path blog.  But it brought back to mind the great Yogi Berra quote that “it ain’t over ’til it’s over.”

We’ve done lots of deals over our 18 year existence.  Something like 12 or 13 acquisitions and 5 spin-offs or divestitures.  And a very large number of equity and debt financings.

We’ve also had four deals that didn’t get done.  One was an acquisition we were going to make that we pulled away from during due diligence because we found some things in due diligence that proved our acquisition thesis incorrect.  We pulled the plug on that one relatively early.  I’m sure it was painful for the target company, but the timing was mid-process, and that is what due diligence is for.  One was a financing that we had pretty much ready to go right around the time the markets melted down in late 2008.

But the other two were deals that fell apart when they were literally at the goal line – all legal work done, Boards either approved or lined up to approve, press releases written.  One was an acquisition we were planning to make, and the other was a divestiture.  Both were horrible experiences.  No one likes being left at the altar.  The feeling in the moment is terrible, but the clean-up afterwards is tough, too.  As one of my board members said at the time of one of these two incidents – “what do you do with all the guests and the food?”

What I learned from these two experiences, and they were very different from each other and also a while back now, is a few things:

• If you’re pulling out of a deal, give the bad news as early as possible, but absolutely give the news.  We actually had one of the “fall apart at the goal line” deals where the other party literally didn’t show up for the closing and never returned a phone call after that.  Amateur hour at its worst
• When you’re giving the bad news, do it as directly as possible – and offer as much constructive feedback as possible.  Life is long, and there’s no reason to completely burn a relationship if you don’t have to
• Use the due diligence and documentation period to regularly pull up and ask if things are still on track.  It’s easy in the heat and rapid pace of a deal to lose sight of the original thesis, economic justification, or some internal commitments.  The time to remember those is not at the finish line
• Sellers should consider asking for a breakup fee in some situations.  This is tough and of course cuts both ways – I wouldn’t want to agree to one as a buyer.  But if you get into a process that’s likely to cause damage to your company if it doesn’t go through by virtue of the process itself, it’s a reasonable ask

But mostly, my general rule now is to be skeptical right up until the very last minute.

Because deals are not done until they are done.

More Good Inc.

Last year I was pleased and proud to write about our debut on the Inc. 500 list of America’s fastest growing companies.  At that time I wrote that “Now our challenge, of course, is STAYING on the list, and hopefully upping our ranking next year!”  Well, I am again please and proud to announce that we, in fact, stayed on the list.  (You can read all the Inc. coverage here and see our press release about the ranking here.)

Unfortunately, we didn’t make the second part of our goal to up our rank.  But, we did up our growth – our three-year revenue growth rate was 18% higher than last year.  This is a testament to the hard work of our team (now 150 strong!) and wouldn’t be possible without the support of our many great clients (now 1,500 strong!).  Most importantly, we see no end in sight.  In fact, 2008 promises to be an even bigger year for us as we poise for continued growth.  By the way, would you like to be part of a team that has now ranked as one of America’s fastest growing companies two years in a row?  Check out our Careers page and join the team that is advancing email marketing, one company at a time.

The Gift of Feedback, Part II

I’ve written a few times over the years about our 360 feedback process at Return Path.  In Part I of this series in early 2008, I spelled out my development plan coming out of that year’s 360 live review process. I have my new plan now after this year’s process, and I thought I’d share it once again.  This year I have four items to work on:

1. Continue to develop the executive team.  Manage the team more aggressively and intentionally.  Upgrade existing people, push hard on next-level team development, and critically evaluate the organization every 3-6 months to see if the execs are scaling well enough or if they need to replaced or augmented
2. Formalize junior staff interaction.  Create more intentional feedback loops before/after meetings, including with the staff member if needed, and cultivate acceptance of transparency; get managers to do the same.  Be extra skeptical about the feedback I’m getting, realizing that I may not get an accurate or complete picture
3. Foster deeper engagement across the entire organization.  Simplify/streamline company mission and balanced scorecard through a combination of deeper level maps/scorecards, maybe a higher level scorecard, and constant reinforcing communication.  Drive multi-year planning process to be fun, touching the entire company, and culminating in a renewed enthusiasm
4. Disrupt early and often, the right way.  Introduce an element of productive disruption/creative destruction into the way I lead, noting item 2 around feedback loops

Thanks to everyone internally who contributed to this review.  I appreciate your time and input.  Onward!