I help mentor CEOs on executive hiring all the time. One common refrain I hear when we’re talking about requirements for the job is about something I like to call The Mythical Playbook. If I only had the exec with the right playbook, thinks the hiring CEO, all my problems in that executive’s area would be magically solved.

I once hired a senior executive with that same mentality. They had the pedigree. They had taken a similar SaaS company in an adjacent space from $50mm to $250mm in revenue in a sub-group within their functional area. They had killer references who said they were ready to graduate to the C-level job. They had The Playbook! 

Suffice to say, things did not go as planned. I ignored an early sign of trouble, at my own peril. The exec came to me with a new org chart for the department, one with 45 people on it instead of the 20-25 who were currently there. I believed the department was understaffed but was surprised to see the magnitude of the ask. When I pushed back in general, the response I got was “I plan to overspend and overdeliver.” Hmm, ok. I don’t mind that, although a more detailed plan might be useful.  

Then I pushed back on a specific hire, pointing to a box in the org chart with a title that didn’t make sense to me. The response I got was “Yeah, I’m not entirely sure what that person does either, but I know I need that, trust me.” Yikes. 

There are two reasons why The Playbook is mythical. 

The first reason there’s no such thing as a Playbook for executives is that every situation is different. No two companies are identical in terms of offering or culture or structure. Even within the same industry, no two competitive landscapes are the same at different points in time. If life as a senior executive were as simple as following a Playbook, people would make a zillion dollars off publishing Playbooks, and senior executive jobs would be easier to do, and no one would get fired from them.

Now, I’m not saying there isn’t value in analogous experience. There is! But when hiring an executive, you’re not solely looking for someone who claims to know all the answers based on previous experience. That is a recipe for blindly following a pattern that might or might not exist. The value in the analogous experience is in knowing what things worked, sure, but more importantly in knowing when they worked, why they worked, under what conditions they worked, what alternatives were considered, and what things fell apart on the road to success. A Playbook is only useful if it can be applied thoughtfully and flexibly to new situations.

The second reason there’s no such thing as a Playbook when it comes to hiring executives is that the person who might have written the Playbook is actually not available for your job. Most CEOs start a search by saying, “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 you. They have made a ton of money, and they have moved beyond your job in their career progression. What you want is 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 are much harder to find. And when you find them, they don’t have the Playbook. They may have seen a couple chapters of it, but that’s about all.

In the end, the department I referenced above was more successful, but not because of adherence to the new exec’s entire Playbook. The Playbook got the department out over its skis – we overspent, but we did not overdeliver. The new exec ended up leaving the company before they could implement a lot, and that person’s successor ended up refocusing and rightsizing the department. That said, the best thing the department got out of the exec with the Playbook was their successor, which was huge — one element of a strong exec’s Playbook is how to build a machine as opposed to just playing whack-a-mole and solving problems haphazardly.

(Note – I am using the singular they in this and in other posts now, as Brad. Mahendra, and I chose to do in Startup Boards. I don’t love it, but it seems to be becoming the standard for gender neutral writing, plus it helps mask identities as well when I write posts like this.)

Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, by Sarah E. Brown, is an amazing book – and one that fits really well with our Startup Revolution series, in particular our book Startup CXO.

I kept thinking as I was reading it that it was the other side of the proverbial coin…that Startup CXO was about the details of each executive job in a company…but Sarah’s book is about the things common to ALL executive jobs – how to get them, how to succeed at them, essentially how to BE an executive. I read it front to back in a single day one weekend and loved it.

Some of the most insightful moments in her book are:

• Why big company executives who join startups often struggle
• How to get promoted by proactively doing the next job – act “as if” – while still excelling at your current job
• The importance of managing to the CEO’s preferred work style (personally…I’d debate this – I think CEO’s should manage to their CXOs’ work styles or at least make it a two-way street, but her point is very valid!)
• Why executives shouldn’t just up and quit with “two weeks’ notice” but that executives also need to be mentally prepared to be shown the door when they resign
• The importance of getting your hands dirty and not being “above” doing the work of your team
• Mastering the art of data-driven storytelling

Sarah quotes a number of CEOs throughout the book who I know and respect, from Nick Mehta at Gainsight to Mindy Lauck at Broadly. It was fun to read the book and see a number of very familiar names in it along the way.

Sarah and I did an interesting format – sort of a “dueling fireside chat” about our respective books on a webinar last fall. We had a fantastic conversation that could have gone on for hours. If you’re an executive – or an aspiring executive – you should go read her book.

I have an end of year work routine that’s a pull-up and self-assessment. I’ve been doing this for years, and I’ve written about its evolution in Part I and Part II of this series.

I’ve always taken a few minutes at this time of the year to ask myself these four questions:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

If I answer at least 2.5 of these questions as yes, I feel like things are on track. If I am below that, or even at 2.5 sometimes, it’s time for a rethink of what I’m doing or how I’m doing it.

I was having lunch with my friend Bryton, the CEO of Aquabyte, a few weeks back, and that conversation spurred on a 5th question, which I’ll now add to my end of year routine:

• Am I excited about what I’m doing?

I’ve realized now that I’m over two years into the journey at Bolster that there’s a significant value in being really into the subject matter of the business. I thought I was at Return Path…but now I realize that I wasn’t nearly as excited about what I was doing as I could have been. Our work at Bolster of helping founders be more successful is more personally meaningful to me than solving email deliverability challenges. That work had real impact on the world…but I just wasn’t into it as much.

And that makes a big difference in answering the general question of “Am I on track?” at the end of the year. I’ll skip next week and see you all in 2023. Happy New Year and Happy Holidays, everyone!

(This is the third post in the series… The first one When to Hire your first CMO is here, and What does Great Look Like in a CMO is here).

 In Startup CXO I wrote that I always think that the French Fry Theory can be applied to many things, usually other food items. The French Fry Theory is the idea that you always have room to eat one more fry and in my case I always do. But the same idea applies to marketing because you can always do “one more thing.” One more press release. One more piece of collateral. One more page on the corporate web site. One more newsletter. Trade show. Webinar. Research study. Ad. Search engine placement. Vendor. System. Speech. Take your pick.

The world we operate in is so dynamic that marketing (when done well) is nearly impossible to ever feel like you’re completely on top of and it’s near impossible to get closure. There’s always more to be done, and the trick to doing it well is knowing when to say “no” as much as when to charge into something. In my experience, CMOs who aren’t scaling well past the startup stage are the ones who typically do one or all of the following.

First, they’re stuck in “french fry mode” and treat all tasks like french fries. They focus on task execution (eating the next fry) and can’t pull up to think about whether they’re doing the right thing (should they be ordering another plate of fries?) and they are simply not scaling. If your CMO is constantly putting out fires that’s a sign that they may be too task-oriented and not strategic enough.

 Another sign that your CMO isn’t scaling is if they report on activity as opposed to outcomes. This is related to my prior point.  When all the world is a task list, then report-outs are just volumes of tasks but tasks are not the same as productivity or results.  I’m not sure why marketing ended up like this, but it’s frequently the only function in the company that spends time producing beautiful reports on all the stuff they do.  It probably comes from years of working with agencies who report like that to justify client spend.  Regardless, can you imagine seeing reports on activity instead of outcomes from other departments? Do you really need the report from the CFO that talks about how many collections calls the team made as opposed to reporting on bad debt? Or a report from the CRO talking about how many meetings a rep had with no mention of pipeline or closes – seriously?  No thank you.  CMOs who can’t link activity to outcome with a focus on outcome are not scaling with the job and for all you know they may be rearranging the chairs on the Titanic.

A final sign that your CMO isn’t scaling is if they spend disproportionate amounts of time on creative or agency work.  That’s the glamorous and fun part of marketing, for sure.  Having made TV commercials as a head of marketing when I was at MovieFone, I can attest to that.  But even if you’re a big B2C marketer with a lot of agency and creative spend, while you should be supervising that work, spending all your time on it is a sign that you’re not interested in all the other, well, french fries.

Marketing is becoming increasingly complex and differentiated, and it can easily be a service center as opposed to a strategic function. I don’t think that’s ideal, but that may be how a company decides to run it. But even if it is a service function your CMO needs to able to create space in their day for thinking and analysis, they need to be strategic, and they need to be able to stop doing “one more thing.”

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

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 is the second post in the series… the first one When to Hire your first Chief Marketing Officer is here).

Whether you have someone in your company that can level up to greatness or you need to bring in a CMO, the characteristics and skills of a great CMO you should aspire to include some of the following.

A great CMO understands that the marketing budget starts with drivers and business results and works backwards in a modular way to spend, not the other way around. Yes, they will get some resources but rather than spend that money to fill in the gaps on their team to make the Marketing function strong or powerful, they’ll look at the business needs and drivers. They understand what the business needs to achieve — the sales plan — then what the funnel looks like. With that information a great CMO will then know what marketing levers they can pull to both optimize the funnel and make sure the funnel is full.  So, they build the plan in a modular way. By doing that, if the budget needs to be trimmed, they can ask the right questions and easily trim. If you start the other way—if you start by looking at the budget and filling gaps and needs, you can get into a situation where you’re looking for ways to keep people busy, shifting them to where they’re needed but where they might not have skills to make an immediate impact, or you’re always scrambling to keep up with developments in sales and the funnel that you didn’t see. A great CMO will always start with the drivers and business needs and be conservative with resources and a modular approach helps to do that.

A second characteristic of a great CMO is that they make spend decisions based on a deep understanding of data, not on a hunch or because “that’s what’s always worked.”   Even in traditional B2C businesses that make heavy use of traditional non-addressable media (like print, outdoor, radio, and TV) – even in those businesses, today everything can be tested and measured to some degree.  A strong CMO is one who starts every answer with “let’s look at the data,”and if the data doesn’t exist, they’ll create metrics and measures to approximate an answer.

A great CMO will behave like a CEO in terms of being able to orchestrate the different pieces and parts of their organization.  Just as a CEO has to manage a litany of disparate functions, so too do CMOs have to manage a litany of disparate channels, they have to manage up and down the organization, and sideways, too.  Gone are the days when CMOs were either “brand or direct” or “online or offline.”  Today, the average CMO has to be able to manage 20+ different channels.  The level of complexity and number of points of failure for the job has exploded.  A great CMO handles this with the fluidity that the CEO handles moving from a Sales Pipeline meeting to a Product Roadmapping exercise. 

The final characteristic of a great CMO is that they get away from their ivory tower–they spend time in-market and in-product, not just time looking at data, budgets, and reports.  Given all the responsibilities around multi-channel orchestration, systems, budgeting, and execution in general, it can be very easy for a CMO to operate 100% from behind the desk.  The great ones want — need — to be out in the field, attending sales calls, partner meetings, events, serving as executive sponsor on some key accounts; in general, collecting primary data on the company’s products and brand.

 A great CMO can be cultivated from within your company and it’s not necessary to look outside, but regardless of how you get a CMO, the great ones will have the characteristics and traits listed here.

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

I was excited to read Launchpad Republic: America’s Entrepreneurial Edge and Why It Matters, by Howard Wolk and John Landry the minute Brad sent it to me. I love American history, I love entrepreneurship, and I’m deeply concerned about the health of our country right now. I have to say…on all fronts, the book did not disappoint!

The authors make several points, but the one that sets the tone for the book is that like our country’s origins and culture in general, entrepreneurship is itself rebellious. It’s about upstarts challenging the status quo in some way or other with a better way to do something, or with a new thing. The balance between protecting private property rights and allowing for entrepreneurs to fail and to disrupt incumbent leaders is what makes America unique, especially compared to the way European business culture has traditionally operated (consensus-oriented) and the way China operates (authoritarian).

I loved how the authors wove a number of business history vignettes together with relevant thru lines. Business in Colonial times and how Alexander Hamilton thought about national finances may seem dusty and distant, but not when you see the direct connection to John D. Rockefeller, IBM, GE, Microsoft, or Wendy Kopp.

The book was also a good reminder that some of the principles that have made America great and exceptional also underly our successful business culture, things like limited government, checks and balances within government and between government and the private sector, and decentralized finance.

Without being overly political, the authors also get into how our political and entrepreneurial system can and hopefully will tackle some of today’s more complex issues, from climate change to income inequality to stakeholder capitalism.

At the heart of all of it is the notion that entrepreneurs’ creativity drive America forward and are a leading force for making our country and our economy durable and resilient. As a career entrepreneur, and one who is now in the business of helping other entrepreneurs be more successful, this resonated. If you’re a student of American history…or a student of entrepreneurship, this is a great read. If you’re both, it’s a must read.

(Post 1 of 4 in the series of Scaling CMOs)

Unlike some of the other teams in a startup, the marketing function often has a few people carrying out various tasks and you’ll find that there is at least a medium sized and quite busy marketing department—even at the earliest startup stages. You could operate this way for quite some time and it’s common to have a marketing team with multiple mid-level leaders well before there is a seasoned leader at the helm.  One of those leaders may be a VP of Marketing and, depending on the nature of the company, that VP is likely someone with a specialized area of focus within marketing (brand, digital, event, etc.) who has some working knowledge of the other areas.

You might be able to keep going with a VP of Marketing for quite some time, but you’ll know it’s time to hire a CMO when you run into a series of problems or challenges that ought to be easy to get done. For example, if you begin to think that no one in your company but you knows how to orchestrate a successful product launch it might be time to hire a CMO. A successful product launch requires cross-functional and cross-team effort and if you don’t have a broadly skilled Marketing manager, you’ll end up doing a lot of the work yourself. It doesn’t have to be a product launch that is the motivating factor, though, because it could be any situation where you find that you are spending too much of your own time managing smaller pieces of marketing because your marketing leader isn’t experienced enough across all of the function’s many sub-disciplines. So, the first sign that you need to hire a CMO is if you’re basically doing the CMO job as the CEO.

Another telltale sign that you need to hire a CMO could stem from your inability to answer simple questions from your board, like “How would you spend an extra $2mm in marketing if you had it?” Or, “What would you cut if you had to reduce your marketing spend by 50%?” These are the scenarios that a CMO spends a lot of time thinking about and they’ll have a whole slew of answers and ways to get to the next level, or ways to be more efficient with the marketing dollars they do have. If it’s a struggle for you to cobble together a good answer, or if you don’t know how to get to an answer on questions like these, it’s time to hire a CMO.

A fractional CMO can make a big impact in your company immediately and that might be the way to go if you have a generalist marketing manager or director who has strategic inclinations but not enough experience operating as a strategic executive. A fractional CMO would be able to mentor the person who just needs a little more supervision to “level up.” On the other hand, if you have a few junior leaders of marketing sub-functions, none of whom is experienced enough to coordinate activities across groups, but you don’t have enough complexity or scale for a full-time CMO, a fractional executive can come in to help with coordination and put some processes in place until you need a full-time CMO. 

Marketing is the key function in building your brand, reaching out to customers, and creating higher levels of engagement, and while there are tactical aspects that can be handled with competent managers of various sub-functions, you’ll need to think about hiring a Chief Marketing Officer when lots of coordination is required and you find yourself driving a lot of it.

You can find this post on the Bolster Blog here)

(Post 4 of 4 in the series on Scaling CROs – other posts are, When to Hire your First Chief Revenue Officer, What Does Great Look like in a Chief Revenue Officer and Signs your Chief Revenue Officer isn’t Scaling)

Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent.

One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events.  Particularly if you’re a B2B company that engages with clients during the sales process, you’ll probably find yourself at a lot of client meetings and events, either internal or external.  Your CRO will be there, too, which gives you a great opportunity to spend large blocks of time together in transit, or a good deal of time together socially. One thing we learned during the work-at-home pandemic is just how much time we save by not traveling.  So when life resumes to normal, why waste time in an Uber or on a plane when you can have a deep strategic conversation or even a personal/social one with one of your senior executives? Of course, you have to actually be more proactive in meeting with your CRO since you won’t have events that naturally bring you together, but I’ve found that the early morning time in the hotel gym or late-night drink in the lobby bar before heading up to bed now translates to time I can have with my CRO. 

Another way to engage with the CRO is In a Weekly Forecast meeting.  Jeff Epstein, former CFO of Oracle, was one of my long-time board members at Return Path and he helped us architect a new core business process once our sales team got large and mature and geographically disparate enough that it was hard for us to have a solid forecast.  Both me and our CFO engaged in the Weekly Forecast meeting and because of that we forced the discipline of a good roll-up of all regions and business units. The CRO and all sales managers attended and knew that we were paying attention to the numbers and trends and asking tough questions. Our attendance was a forcing function for the CRO so that they organized a pre-meeting the prior day with all teams and units to prepare, and that in and of itself had a cascading effect through the organization of adding discipline, rigor, and accuracy to the forecast.  It also made me a lot more empathetic to my CRO’s issues with respect to the sales leadership team.

Finally, the other way that I engaged with the CRO was ad hoc, either internally or in-market.  My most successful heads of sales have been good at winding me up and pointing me at things as needed, whether that means getting on a plane or Zoom to help close a deal or save a client, or doing a 1:1 mentoring session with a key employee. So, not all interactions with the CRO have to be initiated by the CEO, and a great CRO will use the CEO, leverage their time, when it’s needed.

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

In 2005, I wrote a post called Unfolding the Map in which I looked at these two seemingly opposing philosophies from successful entrepreneurs:

• If you don’t have a map, you can’t get lost
• If you don’t have a map, you can’t get where you’re going

and tried to combine them when thinking about product roadmapping. The same contradiction and combination could be applied to anything, including coaching and development.

That’s why I was excited to read my friend Matt Spielman’s new book, Inflection Points: How to Work and Live with Purpose. Matt worked at Return Path twice over the years — first as employee #3 (more on that in a minute) and then over a decade later as CMO. We live near each other and know each other’s families. I’ve been lucky enough to see his career unfold and develop into what it is today, a flourishing coaching business called Inflection Point Partners that helps clients tremendously…and that also feeds Matt’s soul.

When I first met Matt and he joined me and Jack to launch Return Path in 1999, he was fresh out of business school and focused on sales and marketing from his prior career in investment banking. Our idea was that he would do the same for us as we got our product in market. But as I started focusing more on what kind of company we wanted to build and how to get there, Matt became my leading thought partner on those topics. When we got to about 25 people, he and I created a new role for him — head of Human Capital and Organization Development. While a bit clunky, that title meant that Matt was the principal person helping me create at small scale what we later branded our People First philosophy. That philosophy and the practices we developed out of it led to 20 years of a strong track record of investing in people and helping over 1,300 colleagues grow their careers by being simple, actionable, and broad-based in the way we handled feedback and development planning. This started back in 2000.

Matt’s book puts the ethos that I saw percolating over 20 years ago into a tight framework around his coaching methodology of the GPS (Game Plan System). The book is short and sweet and walks through both the philosophy and the framework in accessible terms. And while it’s true that you have to be open to new ideas, open to serendipity, and go with flow sometimes…it’s also true that if you have specific goals in mind, you are unlikely to achieve them without a focused effort.

I’ve written a lot about coaching lately between The Impact of a Good Coach and another recent post about a strong coaching framework about intentionality in Russell Benaroya’s book. In that second post, I noted that “While I have become less and less of a life planner as I’ve gotten older under the headline of ‘man plans, God laughs,’ I am a huge believer in being intentional about everything. And that pretty much sums up Matt’s book: If you don’t have a map, you can’t get where you’re going.

(Post 3 of 4 in the series of Scaling CRO’s- the other posts are When to Hire your First Chief Revenue Officer and What does Great Look like in a Chief Revenue Officer).

If you’ve hired a “great” CRO (see previous post) you might think that you’re set for a long time and that the great CROs are also able to scale. Not always, and you’ll have to check to make sure that your CRO is scaling and growing as much as your company. I’ve found that there are several telltale signs that your CRO isn’t scaling and fortunately, they are easy to spot and easy to correct.

First, if your CRO gravitates to being an individual contributor sales rep and focuses on closing big deals instead of mentoring sales managers and sales reps to do that work on their own, that could be a sign that your CRO lacks the confidence to be a true executive.  The risk in being an executive is not that you can’t do the work, it’s that you don’t trust your team to do the work. To be clear, sometimes the role of a sales leader (or a CEO) is to swoop in and help close a big deal–sometimes.  But CROs who can’t shake their addiction to closing deals almost never build enough of that muscle into their organization and end up creating unhealthy dependency on themselves. Worse, they do not create a career path for others in the sales organization to learn and take risks. 

Second, I’ve found that a CRO who gets the sales commission plans out in March or April instead of January or early February is maybe someone who can’t scale.  While it’s true that, in a lot of businesses, it’s very difficult to get sales commission plans out until after the year starts, getting them out after late February is a sign that your CRO doesn’t have enough of a grip on numbers, isn’t partnering effectively with finance, doesn’t care enough about their people, or isn’t good at prioritizing the important over the urgent when needed. Obviously, if this happens once it’s not a big deal, but if you find that the CRO is the last person on your team to get their plans together year after year, that’s a telltale sign that maybe they’re in over their heads. You might hear them say, “They’ll all be fine, they know I’ll take care of them, the plan is a lot like last year’s.” That might be okay for the majority of the sales team but it won’t be good enough for the best reps who are constantly doing Sales Math in their heads.  It’s a lot easier to mentor or CRO, or find a new one, than to build a new team of dedicated sales reps.

Finally, a sign that your CRO isn’t scaling is if they regularly deliver surprises at the end of the quarter – both good and bad surprises.  A “surprise” every once in awhile is not a big deal, but regular surprises are a big deal and that tells you something important about the CRO: They might be incapable of scaling and the surprises are coiming because your CRO doesn’t have a good grip on the pipeline and in particular on larger deals. Either they don’t have a grip on the pipeline or they are bad at managing expectations; or both!

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