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)

This was a catchy title I caught in our shared Kindle library at a moment when I wasn’t connected to wifi and had nothing to read. Thanks to Mariquita for buying it…it was a good read.

The book is funny, irreverent, and deep. It speaks a lot about pain and failure and how those can help create resilience. It is also chock full of great anecdotes including a particularly memorable one about Pete Best, the original drummer for the Beatles who got fired by the rest of the band on the eve of their becoming famous.

Here’s one particularly representative quote:

Pain is an inextricable thread in the fabric of life, and to tear it out is not only impossible, but destructive: attempting to tear it out unravels everything else with it. To try to avoid pain is to give too many fucks about pain. In contrast, if you’re able to not give a fuck about the pain, you become unstoppable.

Every founder would benefit from reading this book. It won’t stop you from giving a f*ck about everything (it can’t), but it might give you a couple tools for not giving a f*ck about some things, which would clear up some mental capacity for other more important things!

Boards That Lead, by Ram Charan, Dennis Carey, and Michael Useem, was recommended to me by a CEO Coach in the Bolster network, Tim Porthouse, who said he’s been referring it to his clients alongside Startup Boards. I don’t exactly belong in the company of Ram Charan (Brad and Mahendra probably do!), so I was excited to read it. While it’s definitely the “big company” version to Startup Boards, there are some good lessons for startup CEOs and founder to take away from it.

The best part about the book as it relates to ALL boards is the framework of Partner, Take Charge, Stay out of the Way, and Monitor. You can probably lump all potential board activities into these four buckets. If you look at it that way…these are pretty logical:

• Monitor – what you’d expect any board to do
• Stay out of the Way – basic execution/operations
• Partner – strategy, goals, risk, budget, leadership talent development
• Take Charge – CEO hiring/firing, Exec compensation, Ethics, and Board Governance itself.

There was an interesting nugget in the book as well called the Central Idea that I hadn’t seen articulated quite this way before. It’s basically a statement of what the business is and how it’s going to win. It’s about a page long, 8-10 bullet points, and it includes things like mission, strategy, key goals, and key operating pillars that underlie the goals. It basically wraps up all of Lencioni’s key questions in one page with a little more meat on the bones. I like it and may adopt it. The authors put the creation of the Central Idea into the Take Charge bucket, but I’d put it squarely in the Partner bucket.

Other than that, the book is what you’d expect and does have a lot of overlap with the world of startups. Its criteria for director selection are very similar to what we use at Bolster, as is its director evaluation framework. The book has a ton of handy checklists as well, some of which are more applicable than others to startups, for example Dealing with Nonperforming Directors and Spotting a Failing CEO.

All in, a good read if you’re a student of Boards.

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.

I’m fascinated with this topic and how it’s evolving in society. In Part I, a couple years ago now, I changed my long-held point of view from “CEOs should only wade into politics when there’s a direct impact on their business” (things like taxes and specific regulations, legal immigration) — to believing that CEOs can/should wade into politics when there’s an indirect impact on business. In that post, I defined my new line/scope as being one that includes the health and functioning of our democracy, which you can tie to business interests in so many ways, not the least of which this week is the Fitch downgrade of the US credit rating over governance concerns. Other CEOs will have other definitions of indirect, and obviously that’s ok. No judgment here!

I am a regular viewer of Meet the Press on Monday mornings in the gym on DVR. Have been for years. This weekend, Chuck Todd’s “Data Download” segment was all about this topic. The data he presented is really interesting:

58% of people think it’s inappropriate for companies to take stands on issues. The best that gets by party is that Democrats are slightly more inclined to think it’s appropriate for companies to take stands on issues (47/43), but for Republicans and Independents, it’s a losing issue by a wide margin.

To that end, consumers are likely to punish companies who DO take stands on issues, by an overall margin of 47/24 (not sure where everyone else is). The “more likely” applies to people of all political persuasions.

These last two tables of his are interesting. Lower income people feel like it’s inappropriate for companies to take stands on issues more than higher earners, but all income levels have an unfavorable view, and…

…older people are also more likely to have an unfavorable view of companies who wade into politics than younger people, but again, all ages have an unfavorable view

As I said in Part I of this series, “I still believe that on a number of issues in current events, CEOs face a lose-lose proposition by wading into politics,” risking alienation of customers, employees, and other stakeholders. The data from Meet the Press supports that, at least to some extent. That said, I also acknowledge that the more polarized and less functional the government is…the more of a leadership vacuum there is on issues facing us all.

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.

It’s been a big break between posts – as many of you probably know, I moved to Board Chair and left the CEO role at Bolster last summer (it’s now in the very capable hands of my friend and co-founder Cathy Hawley), and I’m now CEO of a super cool AI company called Acrolinx.  So yes, that means I went through a job search – and I found my ultimate job as a result of an inbound cold email from a headhunter!  The rich irony in that as someone who founded an executive search platform is not lost on me.

So when a good friend of mine who is also between CEO gigs and looking at several opportunities asked me the other day “why is this process so slow, and what can I do about it?” I riffed with him on the theme for a bit and thought I’d share my thinking here. 

Why Executive Searches are Slow

My top three reasons on this are pretty varied – there’s no specific theme.

1. Boards aren’t efficient hiring managers. When hiring a CEO, even the best intentioned boards can be slow to move. Frequently they operate with a search committee, and even if there’s a lead director on the search committee or even no actual search committee, by design they need to operate with a high degree of consensus. Organizing five calendars to meet with or debrief on a candidate can take weeks. And a single loud voice saying “no” or “not sure” can paralyze a board. All this is true for a CEO search but can also be true when a less experienced CEO is trying to hire a CXO and needs a lot of Board involvement in the process. At Bolster, we’ve worked on mitigating this by getting the key decision-makers aligned on search criteria at the beginning of the search, prepping interviewers, and creating a scorecard for each candidate that is visible to all decision-makers, but sometimes that doesn’t matter.
   
2. Boards and CEOs often don’t know what they want.  Whether a company is hiring a role for the first time or replacing an executive, they often get to a generic job spec but don’t actually know what they’re looking for. Not all CEOs are created equal. Not all CROs have the same core competencies. At Bolster, we developed a description of role archetypes for each C-suite or Head-or role that helps with this process (eg for a CFO, do you want an Accounting type, a Finance/Ops type, or a Deal type?). But even if a Board or hiring CEO has this level of detail down, it can still be a murky picture, trapped between the company’s past successes and failures on one side and its future needs on the other. Processes move slowly because it take a while for the picture to become less murky – circumstances around the company evolve, or people see how the company operates without this role as others pick up the slack, and therefore the needs of the role shift or come into focus. Sometimes meeting a series of candidates is the only thing that can help drive this focus, and per the first bullet above, this just takes time. If a company has a strong search partner, that may speed things up via quick presentation of calibration candidates.
   
3. There’s no precipitating crisis.  Most companies and departments, most of the time, are not in crisis. A lot of companies can operate without a given executive, even a CEO, for quite some time. Some things done (don’t) get done. Other people rise to the occasion and pick up the most important items. Or the company has hired an interim or fractional executive as a stop gap measure. Without a specific and clear sense of urgency, searches often don’t have a driving force. Sometimes there’s a precipitating crisis like a system outage or massive customer churn or the company running out of cash that can provide that driving force, but that is not the norm.

What Can You as a Candidate Do About It?

The answer is probably “not much.”  But if my own search was any indicator, I’d give you the same advice I give people internally at my company when they ask me how to get a promotion.  My answer is “start doing the job today, don’t wait to actually get the job.”  Obviously a candidate for a CEO role or any other executive role can’t actually start doing the job as an existing employee could start taking on additional pieces of work.  But there are a lot of things you can do to “act as it” and get the hiring Board or hiring CEO’s attention.  For example:

• As a CEO candidate, be a management consultant.  Work on designing a strategy for the company you want to work for.  Do a tremendous amount of homework you can do from the outside – read analyst reports, get stealth demos, do market and customer interviews.  You don’t have to explain what you’re up to in terms of identifying the company.  You can say you’re interviewing for a CEO role in the sector.  Or even that you’re doing market research.  But proactively sending the hiring board a strategy deck and asking for the next meeting is a good way of differentiating yourself as a candidate and potentially accelerating a process.
  
• As a CRO candidate, go try to sell the company’s product.  Do it to a couple “friendlies” (e.g, people who are friends of yours, not active customers or prospects of the company you’re interviewing with) so you don’t tread on the actual business.  But create your own deck.  Get meetings.  Write up your experience.  Sending the CEO or board an email that says “Hey, I have a prospect already in the final stage of the funnel for you, can we work together to close her?” is a sure way to differentiate yourself as a candidate and potentially accelerate a process.

There may be a macro answer here as well.  The market is still choppy, and boards and CEOs are more conservative in most sectors and subsectors than they are in go-go times.  So that may be slowing things down in general and may even make it harder to act as-if.  But that doesn’t mean you can’t try.

(Post 1 of 4 in the series of Scaling CPO’s)

 Most startups don’t have a Chief Privacy Officer and just rely on outside advice from external counsel or a privacy consultant. In Startup CXO our Chief Privacy Officer from Return Path, Dennis Dayman, strongly advocates for privacy to be baked into a startup at the very beginning. Some startups probably don’t have any help in this area at all but given the importance of privacy and security issues today that’s a mistake.

If your startup doesn’t start life with a Chief Privacy Officer you’ll have to heed some warning signs and here are some I’ve picked up over the years. First, you’ll know it’s time to hire a Chief Privacy Officer when you wake up in the middle of the night terrified that you’re going to find your company on the front page of the newspaper or served a subpoena to testify before Congress about a data breach. Even if you’re not waking up in the middle of the night you might be concerned about privacy if you are spending too much of your own time trying to understand what PCI Compliance, or HIPAA, or GDPR means to your business. Or if you really don’t see the connections between your business and privacy issues in general, then a Chief Privacy Officer can be very helpful.

You might get tough questions from your board on what your data breach client communication plan is, and if you don’t have a great answer and aren’t sure how to get to one, then it’s time to think about a Privacy Officer.

A fractional Chief Privacy Officer may be the best option for most startups…forever. Sometimes you can find one fractional executive for both the Privacy and Chief Information Security Officer roles. You probably can’t get by without a full-time leader in this area if you are large (>$50mm in revenue) and are sitting on a massive amount of consumer data, especially if that information involves PII, financial, or health information.  But if that’s not you, a fractional Chief Privacy Officer may be the way to go.  While a fractional executive is similar to an outside lawyer or consultant, an executive has a company title for external credibility and the personal commitment to the organization to ensure compliance. A fractional exeuctive is way more than a consultant since they’ll be able to provide guidance to employees and represent the company as if they were a full-time Chief Privacy Officer.

Not every startup needs a Chief Privacy Officer since you can cover your bases with lawyers or consultants, but if you’re collecting lots of data from jurisdictions across the world you’d be wise to get a Privacy officer, or a fractional executive, sooner rather than later.

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

This is the second post in the series…. the first one When to hire your first Chief People Officer is here).

While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything illegal, discriminatory, or harassing, you’ll end up in legal trouble and you’ll lose—big time. So, it’s not enough, if you’re expanding rapidly, to “just get a Chief People Officer,” you need to hire a great Chief People Officer and I have found that great Chief People Officers do three things particularly well:

The most important characteristic or attribute of a great Chief People Officer is that they believe their function is strategic. In Startup CXO Chief People Officer Cathy Hawtrey wrote about the ways in which HR/People can be a strategic function and not just a tactical corporate function.  It’s true of most functions, but for whatever reason, (likely past experience), HR leaders frequently don’t view themselves or their functions as strategic, which is not only a huge missed opportunity but maybe says something more important about the confidence level of the Chief People Officer.  If that’s their frame of reference, then they will likely be tactical managers, they’ll keep the trains running on time, but you won’t be able to anticipate the changing talent landscape, much less be strategic about it.  If they believe they can move the needle on the business by improving engagement and productivity and efficiency, if they believe they can make the executive team more effective by helping you with team facilitation and coaching…they can do anything.

A second important characteristic of the Chief People Officer is courage—they have the courage to call you (you, the CEO) out on things directly and firmly when they see you doing or saying anything that is a bit off. It could be around language, inclusion, values, authenticity, or anything else, but they don’t let it slide or ignore it. The CPO, along with you, are the principal stewards of the company’s values and culture.  Even the best CEOs benefit from having a watchdog from time to time.

A third critical trait of a great Chief People Officer is that they think about investment in People in terms of ROI.  It’s one thing to run a killer recruiting function and fill seats efficiently, with high quality, as asked.  It’s an entirely different thing to start the recruiting process by asking if the role is needed, at that level and compensation band, or whether there are other people, fractional people, contractors, or shifts in lower value activities that could be put to work instead.  Only heads of People with deep understandings of the business can transform the function from a gatekeeper/”no” role into a business accelerator.

A great Chief People Officer is all of these things—strategic, courageous, and financially astute. Above all, great Chief people Officers know that they are the role model within a company and that their behavior, their language, their inclusiveness is setting the tone and providing a template for others to follow. 

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

(This is the fourth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, and 3.)

Monday, March 23, Day 7

• Wellness screening – put hot cup of coffee against my temples – now finally the thermometer works (although I can’t say that it gives me a high degree of comfort that I have figured out a workaround!)
• Furious execution and still backlog is growing no matter how much I do – thank goodness team is growing.  Never seen this before – work coming in faster than I can process it, and I am a fast processer. Inbox clean when I go to bed, up to 75 when I wake up, never slows down
• Private sector explosion – this guy can print 3D swabs – but are they compliant?  This guy has an idea for cleansing PPE, this guy can do 3D printing of Ventilator replacement parts, etc.  How to corral?
• Corporate Volunteer form is up – 225 entries in the first 12 hours – WOW
• Congressmen and Senators – people contact them, so they want to help, they want to make news, not coordinated enough with state efforts
• Jay Want – early diagnosis losing sense of smell – low tech way to New Normal
• Coordination continues to be key – multiple cabinet level agencies doing their own thing while multiple private sector groups are doing their own thing (e.g. App – “everyone thinks they’re the only people who have this idea”)
• Mayor of Denver just announced lockdown, I guess that trumps the state solution in town, maybe it’s ok since that just leaves rural areas a bit fuzzier
• Need to revise OS – team is about to go from 3 to 9, private sector spinning up
• Brad OS and State employee OS are different – Slack/Trello/Zoom are not tools state employees are familiar with or can even access.  Now what?
• Kacey insists the team works remotely other than leaders and critical meetings so we can role model social distancing.  GOOD CALL
• One of our private sector guys goes rogue on PR, total bummer – this part (comms) about what we are doing could be more coordinated for sure, but not a priority
• Lots of texts/call with Jared, such a smart and thoughtful guy, really interesting

Tuesday, March 24, Day 8

• Been a week, feels like a month
• Fluid changes to both OS for team and OS for private sector group
• Zoom licenses – state will take a couple weeks to procure them, gotta work around it with Brad
• Slack app won’t get through the firewall.  Maybe IT’s supervisor can do us a favor?
• Comp – interesting expedited process – normally takes 65 days to get approval for temps, today we got it done in an hour!  Comp levels seem incredibly low. But we got done what we needed to get done
• Some minor territorial conflicts with state tech team and our private sector tech team.  Will have to resolve. Surprising how few of these there have been so far given that our team is new and shiny and breaking rules
• Big new Team meeting for first time with Sarah in lead, Red/Yellow/Green check-in (I like that – may have to borrow it!)
• Starting to feel obsolete – love that!  Sarah crushing it, totally feels like the right leader, need to make sure she has enough support (might need an admin?)
• Also…maybe I’m not feeling well?  A little worried I am getting sick. Hope that’s not true, or if it is, hope it’s not the BAD kind of sick.  Going to go work from hotel rest of afternoon
• Call with Jared – concern about managing state’s psychology – testing and isolation services
• Prep for press conference tomorrow

Wednesday, March 25, Day 9

• Woke up feeling awesome – phew – hopefully that was just fatigue or stress induced
• Sarah drowning a bit, feels like me on my 3rd day so makes sense
• Reigning in and organizing private sector seems like a full time job.  We are going to recruit my friend Michelle (ex-RP) to come work with Brad on volunteer management. HALLELUJAH!
• Whiteboard meeting with Kacey holding up her laptop so they can see it on Zoom – hilarious – technology not really working, but we are making the best of it
• State role – facilitate alt supply chain to hospitals since normal chain is broken…also maintain emergency state cache – complex but makes more sense now
• More territorial things starting to pop up with state government…processing volunteers
• Comms overload – here comes the text to alert you to the email to alert you to the phone call
• This team/project is clearly a case of finite resources meets infinite scope and infinite volunteer hand-raising
• Gov press conference – issues Stay at Home order through April 11 (interesting, that wasn’t in the version of the talking points I saw several hours before)
• Meeting some of our new team members.  I can’t even keep up with them, I think we’re up to 15+ now.  Kacey and Kyle are recruiting machines and all these people’s managers are just loaning to us immediately.  Love that.
• Amazingly talented and dedicated state employees – seem young, probably not paid well, but superior to private sector comprables in some ways 
• Talk with Kacey and Sarah about staff/not drowning
• Kacey feels like Sarah is doing a great job, so she cleared me to go home (wouldn’t have gone without her saying ok, she understands how this whole thing is working way better than I do – I guess that’s what a good chief of staff does!)

Stay tuned for more tomorrow…

(This post also appeared on Bolster.com).

As we wrote in The Gig Economy Executive, the major societal trend to “gig,” or part-time/freelance work, has reached the C-Suite.  We created Bolster to help organize a talent marketplace out of what is mostly an informal economy today – one where VC- and PE-backed companies find trusted freelance executives and consultants from their networks.  

In that earlier blog post, we wrote about the different types of on-demand executive work that C-level executives engage in:  interim, fractional, mentor/coach/advisor, project-based consulting, and board roles.

As we’ve been building Bolster this year, we’ve come to appreciate that not only are there different types of gig economy roles…there are several different archetypes of gig economy executives, too.  While there is a clear common theme of the desire to do some form of freelance, or non-full-time work that cuts across the four types, they are very different in their stage of life and their needs.  These are our four main Member user personae, to use the language of Product Management.

First, there is the In Between Executive.  This is the original concept of our founding investors at High Alpha and Silicon Valley Bank that drove their interest in Bolster.  The In Between Executive is someone who is generally mid-career and used to working in full time C-level roles and is, for whatever reason, between jobs at the moment.  Maybe her company just got acquired and she is taking a break.  Maybe her company restructured her out of a job.  Maybe she needed or wanted to take a break from work for family or health reasons.  Maybe she was just ready to look for a new career challenge.  The In Between Executive is perfectly suited to any of the on-demand executive role types but is a particularly good fit for interim CXO, mentor/coach/advisor, and project-based consulting roles.

Second, there is the Career On-Demand Executive.  The Career On-Demand Executive is usually someone who has had many years of experience as a full-time executive and who is now looking for something more flexible, or who just enjoys more variety in his work.  One of the Career On-Demand Executives in the Bolster network I spoke with early on described her journey to me like this:  she was “between things” when a friend of hers who had moved to France and started a company asked her to come set up her HR Department and run it for 6 months while hiring full-time staff.  She took a month off, lived in Paris for 6 months, took another month off, then started to look for something else like that.  Ooh la la.  Sounds pretty good to me.  The Career On-Demand Executive is a particularly good fit for interim CXO, fractional CXO, and project-based consulting roles.

Next, there is the Not Retired Executive.  When I think of the Not Retired Executive, I think of my Dad, who was a successful technology entrepreneur for 30+ years.  Since he sold his company several years back, he has helped a number of startup CEOs do everything from raise money to build a sales and marketing plan, to manage supply chains.  Sometimes he gets paid in cash as a consultant, sometimes he gets equity as an Executive Chairman.  Sometimes he talks to younger entrepreneurs and helps them out “just because.”  The reality of the Not Retired Executive today, however, is that many people are “not retiring” younger and younger because they’ve made enough money to take a step back from hard-charging full-time jobs.  The Not Retired Executive is perfectly suited to any of the on-demand executive role types.  The ones who are later in their careers and closer to being actually retired are particularly good fits for mentor/coach/advisor and board roles.

Finally, there is the Side Hustle Seeker.  The Side Hustle Seeker is someone who is a full-time executive somewhere but who is looking for additional professional opportunities.  She may be an experienced CMO who is excited about mentoring up-and-coming marketing leaders via a local or industry-based professional organization.  She may be looking for chances to “pay it forward” because someone mentored her along the way, earlier in her career.  She may have accumulated enough experience and wisdom to be ready for her first board of directors seat.  Regardless, she’s someone who is a “high wattage” professional who wants to learn and grow herself by connecting with others outside her day-to-day role.  The Side Hustle Seeker is best matched with mentor/coach/advisor and board roles.

So, what kind of gig economy executive are you, and how can Bolster help you find the kind of work you’re looking for while providing you with tools and resources to simplify your life?  Join Bolster as a member to find out!