(This post, written by my co-founder Cathy Hawley, also appeared on Bolster.com)

The gig economy is a labor market where short-term or freelance roles are more prevalent than permanent positions. It’s generally characterized by having independent contractors rather than full-time positions, but in some locations and for some types of roles, gig workers may be part-time or fixed-term employees.

The gig economy that started with roles like artists, drivers and web designers is quickly expanding to include executive-level roles. There are  a few trends in today’s workplace that are driving this expansion. Startups and scaleups have more flexible, remote-friendly work environments and are looking for creative, less expensive ways of accelerating growth. Executives have shorter average job tenure and are more often displaced or between roles, and they are also interested in the flexibility that gig work can give them.

In a study conducted by MavenLink/Research Now, “The White Collar Gig Economy,” 47% of companies state they are looking to hire contractors to fill management and senior executive roles, including c-suite contractors. At the same time, 63% of full-time executives would switch to become a contractor, given the opportunity. These trends will be accelerated by the current economic downturn and recovery, as some companies have fewer resources, and more executives are displaced.

At the executive level, there are a few different types of roles that could be considered ‘gigs’. The most common two are coaching and project-based consulting.  Coaching or advising, and particularly CEO coaching and advising, has become very prevalent over the last 10 years. The CEO hires a coach who can help them navigate new situations and challenges. Often, CEO coaches stay with a CEO for a number of years, helping guide and support them through the stages of company growth. There are also coaches and advisors for other functional areas to provide similar support for other executives, although more commonly these coaches are hired for specific initiatives. 

Then there  is project-based consulting, where executive-level talent is hired to run a specific project such as reviewing a company’s packaging and pricing, performing due diligence on an acquisition, creating a Diversity, Equity and Inclusion strategy, or creating an investor deck for a fundraising event. This type of consulting isn’t new, and it’s similar to what large consulting firms offer. It seems to be more prevalent now for very senior roles than it ever has been in the past.

But the gig economy for executives now reaches well beyond coaches and consultants.  There are also executives who are hired into interim leadership roles while a company searches for a permanent placement. Some roles take a long time to find the right person, but there’s an urgent need for someone to take on the leadership mantle in the interim. If the interim executive is a good fit, and is open to it, it’s not uncommon for this individual to be considered for the permanent position.  “Try before you buy” works both ways — it can be good for the company and good for the executive, too.

An up-and-coming type of executive gig role is the fractional role. We are seeing this more and more in the last couple of years.  Fractional executives can either be consultants or employees, since the expectation is a long-term relationship, on a part-time basis. For example, 3 days or a certain number of hours per week. The fractional executive is responsible for all functional areas as a full-time executive in that same role. The company may be too small to need (or afford) their level of expertise on a full time basis, but needs more than just an advisor or project consultant. The fractional executive generally remains with a company until the company needs a full-time leader for that function, in which case either the fractional executive goes full-time, or the company hires someone new.  Fractional executives may support more than one client at a time, and may also come with a team of more junior functional experts who can support them to take on more work.

Finally, for our purposes at Bolster, joining a company’s board of directors could be considered taking a ‘gig’ role since it’s not a full-time executive role.  Startups and scaleups need independent directors, and their needs change based on their size, stage and strategy. We see a growing trend of companies contracting with directors for 1 -2 years rather than lifetime service. 

There’s a real opportunity right now for companies to capitalize on the expertise of this talent pool without having to hire them for long-term full time roles, and for executives who want to contribute their skills and expertise without the commitment of a 80-hour work week. Bolster is helping bring these two audiences together in a marketplace that matches on-demand executives with companies who need their services the most. Bolster also provides services for members so they can focus on their consulting rather than their business, and for companies to evaluate their executive teams and boards.

Ratcheting Up Is Hard To Do (or Boiling the Frog, Part II)

I’ve had to ratchet down business several times over the years at Return Path.  Times were tough, revenues weren’t coming as fast as promised, my investors and I were growing weary, the dot com crash, etc. etc.  We had layoffs, consolidated jobs, cut salaries multiple times, made people wear 8 hats to get the job done.  It’s an awful process to go through.

In the last year or so, business has finally started going much better.  We’ve been fortunate in many ways that we’re still around, with products that work really well, with a good customer base, and with good and patient investors and employees, as the business climate has improved.  We’ve grown from 22 people (at our low point) up to almost 75.  But what that has meant for our organization is that we’ve had to quickly "ratchet back up," adding people, adding new functions that were previously one of many hats worn by a single person, operating at a different level.  While ratcheting down is a nightmare, it turns out that quickly ratcheting back up is in many ways just as hard on the organization.

Some examples:

– IT (internal email and servers) has been run by a part-time resource and "off the side of the desk" of our product development engineering department.  Now it is almost completely broken, and it turned out we hired a very talented IT manager, probably about three months too late.

– Staffing up is particularly tough without a dedicated HR function and with a legacy of missed budgets.  HR has been done off the side of the desk of me and my executive assistant, and we can’t keep pace any more with all the recruiting, hiring, training, and development planning.  Now that we feel like we need and can afford more staff, we need to hire an HR manager to handle it all, but we need someone in place and trained today, not three months from now.

– A 22 person company can function brilliantly as a network of Individual Contributors who loosely coordinate with each other.  But now what we need at 75 is a a few hardcore Managers that can build systems and processes so that the whole machine runs smoothly.  We don’t necessarily have those people in-house, and if we bring them in from the outside, I’m left wondering if the Individual Contributors will feel like their years of hard work aren’t appreciated if there’s a new layer of management surrounding them.

I hope we never have to ratchet down again…but part of the reason why now is that I never want to have to ratchet back up, either!

Thanks to my COO and business partner Jack Sinclair for his help with this posting.

Not Dead Yet

Ah Spring.  Flowers bloom.  Love is in the air.  And it’s time for the annual round of “email is dead” articles and blog posts.  With apologies to Monty Python, and on the heels of last week’s fracas about social networking having more users than email, once again I say, email is Not Dead Yet!

Three articles of late are pretty interesting and point out that the trends in online channel usage are far murkier than meets the eye.

First, Sherry Chiger’s story in Direct that One in Five Merchants Shuns Marketing Email has a poor headline for an interesting, data-rich article.  The article should be about how “Four in Five” adopt.  The article has links to a bunch of interesting in-depth reports you can download, but some of the eye-catching stats include the fact that more B2C companies use email than their own web site for marketing (96% vs. 90%); that the #1 use of “if I had more money in my marketing budget, it would go to” is “creating more sophisticated email”; and that email is the “most valuable online strategy,” beating out SEO and materially ahead of Social Media, SEM, sending offline traffic online, affiliate, display, and abandoned shopping cart marketing.

Sherry’s follow up article entitled E-mail and Social Media: The New Chocolate and Peanut Butter

 and Liana Evans’ article in ClickZ, Email Can Be Social Media’s Best Friend, both explain the interplay of email and social media nicely.  You can’t, or at least shouldn’t, have one without the other.  This matches our experience at Return Path, where a number of our largest clients are the biggest social networks.  We always say that “social networking runs on email.”  Look at your inbox sometime and see how many messages are from Facebook, LinkedIn, Twitter, etc., which prompt you to create page views for them, um, I mean, visit their sites.

And of course the recent Morgan Stanley data is somewhat problematic (chart published here among other places).  First, I’m not sure where their base data came from, but I’ve never seen an estimate of worldwide email users that’s only 850MM.  The Morgan Stanley report says there are 1.8B people online worldwide, and there are been stats consistently published over the years that between 80-95% of people online use email.  This report from Radicati has the number of email users worldwide growing from 1.4B last year to 1.9B over the next few years. That sounds more like it.  

There’s no question that people spend more time in social networks and will continue to. They’re more multi-faceted. But that “error” in reporting on number of email addresses pretty dramatically changes the two charts. Plus, don’t you have to have an email account to sign up for most social networks?  And as my colleague Ezra Fischer noted, how the counting works in these two charts is important. For example, I have 2-3 email accounts, but I have 10-12 social network accounts. Am I counted once in each category, or 2-3 in the first and 10-12 in the second? Or worse, once in the first and 10-12 times in the second?

Anyway, every time I write one of these “in defense of email” posts, I get criticized for having too vested an interest in the subject matter to be objective.  If that’s the case, so be it – but who else is going to highlight the positive counterpoints when the buzz is all pointed to the demise of email?

(This is the fifth 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, 3, and 4.)

Thursday, March 26, Day 10

• Sarah continuing to take over and stronger by the day
• Sarah cleared me to go home, only one more person to ask
• Deep deep dive on Mass Testing – so good to spend that time 
• Pretty much got the strategy right – shocking we could get that close with so little public health experience – Kyle awesome – EOC leadership briefing
• That was most of the day
• Some downloads to Sarah and Kacey
• Feeling that two of our project teams are going sideways – that will be a big focus for me tomorrow before I leave
• Quick assignments for tomorrow
• Talked to Jared – he’s good with me going now that Sarah is in place and things are running.  Awesome!

Friday, March 27,  Day 11

• Download with a couple of the project teams to help get them back on track 
• This whole thing is one big exercise in Agile!
• Serendipitously might have found private sector partner for one of the teams in need.  Reminded of George’s great line, “when the student is ready, the teacher appears”
• Gov briefing on mass testing plan
• Spent a lot of the day on strategy/overview/retrospective deck.  Have to review it with Brad and core team members. Gov wants to get it in front of the National Governors Association to share learnings/best practices for the states behind us in this fight
• Gov thankful goodbye
• Brad thank you Haiku – so awesome – “You see things others don’t see”
• FInal team check-in, lots of nice thank yous from people on team
• Close out drinks with Sarah, Kacey, Kyle – persevered despite lack of corkscrew.  Poor Kyle’s shirt looks like he was standing next to a shooting victim
• Incredibly thankful moment with team – really like and care about these people – we’ve done such great work together – 11 days but feels like months and months
• Close out email to Governor and Chief of Staff about team

Saturday, March 28, Day 12

• Check out!  Fly home! Happy to see Mariquita, Casey, Wilson, and Elyse!

Stay tuned for two more wrap-up posts, tomorrow and the next day…

Response to a Deliverability Rant

Justin Foster from WhatCounts, an email service provider based in Seattle, wrote a very lengthy posting about email deliverability on the WhatCounts blog yesterday.  There’s some good stuff in it, but there are a couple of things I’d like to clarify from Return Path‘s perspective.

Justin’s main point is spot-on.  Listening to email service providers talk about deliverability is a little bit like eating fruit salad:  there are apples and oranges, and quite frankly pineapples and berries as well.  Everyone speaks in a different language.  We think the most relevant metric to use from a mailer’s perspective is inbox placement rate.  Let’s face it – nothing else matters.  Being in a junk mail folder is as good as being blocked or bounced.

Justin’s secondary point is also a good one.  An email service provider only has a limited amount of influence over a mailer’s inbox placement rate.  Service providers can and must set up an ironclad email sending infrastructure; they can and must support dedicated IP addresses for larger mailers; they can and must support all major authentication protocols — none of these things is in any way a trivial undertaking.  In addition, service providers should (but don’t have to) offer easy or integrated access to third-party deliverability tools and services that are on the market.  But at the end of the day, most of the major levers that impact deliverability (complaint rates, volume spikiness, content, registration/data sources/processes) are pulled by the mailer, not the service provider.  More on that in a minute.

I’d like to clarify a couple of things Justin talks about when it comes to third-party deliverability services.

Ok, so he’s correct that seed lists only work off of a sample of email addresses and therefore can’t tell a mailer with 100% certainty which individual messages reach the inbox or get blocked or filtered.  However, when sampling is done correctly, it’s an incredibly powerful measurement tool.  Email deliverability sampling gives mailers significantly more data than any other source about the inbox placement rate of their campaigns.  Since this kind of data is by nature post-event reporting, the most interesting thing to glean from it is changes in inbox placement from one campaign to another.  As long as the sampling is done consistently, that tells a mailer the most critical need-to-know information about how the levers of deliverability are working.

For example, we released our semi-annual deliverability tracking study for the first half of 2005 yesterday, which (download the whitepaper with tracking study details here or view the press release here).  We don’t publicly release mailer-specific data, but the data that went into this study about specific clients is very telling.  Clients who start working with us and have, say a 75% inbox placement rate — then work hard on the levers of deliverability and raise it to 95% on a sampled basis, can see the improvements as their sales and other key email metrics jump by 20%.  Just because there’s a small margin of error on the sample doesn’t render the process useless.

Second, Justin issues a big buyer beware about Bonded Sender and other “reputation” services (quotes deliberate – more on that in a minute as well).  Back in June, we released a study about Bonded Sender clients which showed that mailers who qualified for Bonded Sender saw an average of a 21% improvement in inbox delivery rates (range of 15%-24%) at ISPs who use Bonded Sender such as MSN, Hotmail, and Roadrunner.  We were pretty careful about the data used to analyze this.  We only looked at mailers who were clients both before and after joining the Bonded Sender program for enough time to be relevant, and we looked at a huge number (100,000+) of campaigns.  Yes, it’s still “early days” for accreditation programs, but we think we’re off to a good start with them given this data, and the program isn’t all that expensive relative to what mailers pay for just about everything else in their email deployment arsenal.

Finally, let me come back to the two “more on that in a minute” points from above.  I’ll start with the second one — Bonded Sender is an accreditation program, or a whitelist, NOT a reputation service.  Accreditation and Reputation services are both critical components in the fight to improve inbox placement of legitimate, permissioned, marketing emails, but they’re very different kinds of programs (a little background on why they’re important and how they fit with authentication here).

Accreditation services like Bonded Sender work because, for the very best mailers, third parties like TRUSTe essentially vouch that a mailer is super high quality — enough so that an ISP can feel comfortable putting mail from that mailer in the inbox without subjecting it to the same level of scrutiny as random inbound mail.

There are no real, time-tested reputation services for mailers in the market today.  We’re in the process of launching one now called Sender Score.  Sender Score (and no doubt the other reputation services which will follow it) is designed to help mailers measure the most critical levers of deliverability so they can work at solving the underlying root cause problems that lead to low inbox placement.  This is really powerful stuff, and it will ultimately prove our (and Justin’s) theory that mailers have much more control over their inbox placement rate/deliverability than service providers.

Where does all this lead?  Two simple messages:  (1) if you outsource your email deployment to an email service provider, pick your provider carefully and make sure they do a good job at the infrastructure-related levers of email deliverability that they do control.  (2) whether you handle email deployment in-house or outsource it to a service provider, your inbox placement rate is largely in your control. Make sure you do everything you can to measure it and look closely at the levers, whether you work with a third-party deliverability service or not.

Apologies for the lengthy posting.

Scaling Me

Two things have come up over the last couple years for me that are frustrations for me as a CEO of a high growth company.  These are both people related — an area that’s always been the cornerstone of my leadership patterns.  That probably makes them even more frustrating.

Frustration 1:  Not knowing if I can completely trust the feedback I get from deep in the organization.  I’ve always relied on direct interactions with junior staff and personal observation and data collection in order to get a feel for what’s going on.  But a couple times lately, people had been admonishing me (for the first time) when I’ve relayed feedback with comments like, “of course you heard that — you’re the CEO.”

So now the paranoid Matt kicks in a bit.  Can I actually trust the feedback I’m getting?  I think I can.  I think I’m a good judge of character and am able to read between the lines and filter comments and input and responses to questions I ask.  But maybe this gets harder as the organization grows and as personal connections to me are necessarily fewer and farther between.

Frustration 2:  Needing to be increasingly careful with what I say and how I say it.  This comes up in two different ways.  First, I want to make sure that while I’m still providing as transparent leadership as I can, that I’m not saying something that’s going to freak out a more junior staff member because they’re missing context or might misinterpret what I’m saying.  Ok, this one I can manage.

But the tougher angle on this is having unintended impact on people.  Throwing out a casual idea in a conversation with someone in the company can easily lead to a chain reaction of “Matt said” and “I need to redo my goals” conversations that aren’t what I meant.  So I’ve done some work to formalize feedback and communication loops when I have skip-level check-ins, but it’s creating more process and thought overhead for me than I’m used to.

Nothing is bad here – just signs of a growing organization – but some definite changes in how I need to behave in order to keep being a strong and successful leader.

Overload

Fred had a great posting last week called The Looming Attention Crisis.  He talks about how he’s at his limit of trying out new technology and consuming information/feeds.  He’s right — except I’d argue there’s nothing looming about the crisis.  Those of us who were early adopters of RSS (perhaps early adopters in general) are in full Overload mode at this point.

The negatives associated with this problem are pretty clear.  One of my very first postings, Present AND Accounted For, talked about the perils of multitasking on interpersonal relationships; that’s probably the biggest negative to the availability of all this information.  Attention, as Fred says, IS in fact a zero sum game. 

The great problem associated with all of this Web 2.0 stuff is that the web is now much more easily a read/write platform, as opposed to the primary read platform it was in the early days.  So now, everyone can have a printing press — but not everyone should.  And those who do, shouldn’t necessarily feel compelled to use those presses all day, every day.

We need some new tools and services to help reduce the Overload factor quickly.  Tips for better organizing information help (thanks, Whit), but they’re not enough.  We need better keywords and searching of the information that’s out there.  We need better tools to help understand which feeds to read and which to avoid — in other words, ways to figure out who shouldn’t have a printing press.  We need better tools to de-dupe information, or better yet to consolidate duplicate information with a clean list of sources.  We need better integration with mobile devices to scan the information during away-from-desk time.  Most of all, we need all of these tools to be integrated before average users can really adopt.

Maybe all of these tools are out there, and I just to find need more time (somehow) to find and implement them.  I’m sure some entrepreneurs far smarter than I am about Web 2.0 will come up with these things before long…and then of course we’ll hear about them 872 times until we implement their solutions.

(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)

Scaling Frustrations

Two things have come up in spades lately for me that are frustrations for me as a CEO of a high growth company.  These are both people related — an area that's always been the cornerstone of my leadership patterns.  That probably makes them even more frustrating.

Frustration 1:  Worrying that I don't get completely candid feedback from deep in the organization.  I've always relied on direct interactions with junior staff and personal observation and data collection in order to get a feel for what's going on.  But a couple times lately, people had been warning me (for the first time) when I've relayed feedback with comments like, "Of course you heard that — you're the CEO.  People will tell you what they think you want to hear." 

So now the paranoid Matt kicks in a bit.  Can I actually trust the feedback I'm getting?  I think I can.  I always have.  I think I'm a good judge of character and am able to read between the lines and filter comments and input and responses to questions I ask.  But maybe this gets harder as the organization grows and as personal connections to me are necessarily fewer and farther between. I probably need to start recognizing that as the CEO, people may feel uncomfortable being totally open…and it is my job to figure out how to be sure people understand that I do want to hear their voices…unplugged and constructive.

Frustration 2:  Needing to be increasingly careful with what I say and how I say it.  This comes up in two different ways.  First, I want to make sure that while I'm still providing as transparent leadership as I can, that I'm not saying something that's going to freak out a more junior staff member because they're missing context or might misinterpret what I'm saying.  Ok, this one I can manage.

But the tougher angle on this is having unintended impact on people.  Throwing out a casual idea in a conversation with someone in the company can easily lead to a chain reaction of "Matt said" and "I need to redo my goals" conversations that aren't what I meant.  So I'm doing some work to formalize feedback and communication loops when I have skip-level check-ins, but it's creating more process and thought overhead for me than I'm used to.

Nothing is bad here – just signs of a growing organization – but some definite changes in how I need to behave in order to keep being a strong and successful leader.

Is Permission Still Relevant?

My colleague Stephanie Miller wrote a great post on our Return Path blog this week entitled Is Permission Enough? The essence of her argument is:

…permission is not forever…Subscribers opt in and then promptly forget about their actions…Nor is permission a panacea. Opt-in doesn’t replace relevancy and keeping your promises.

And she goes on to give great examples of how marketers abuse permission and a great checklist of times marketers shouldn’t ASSUME permission, which is where the trouble starts.

So I concur — permission is never enough from a sender’s perspective.  But you still have to have it.  Why?  Read on.

I’d like to extend Stephanie’s argument from senders to receivers and question whether permission is as relevant as it once was in terms of how ISPs, filters, and blacklists determine whether or not to block mail.

The argument for permission as a relevant filtering criteria goes something like this:

1. Unsolicited commercial email = evil. It is the true definition of spam.  If I don’t ask for it, you have no right to send it to me.

The argument against permission as a relevant filtering criteria is more nuanced:

1. It doesn’t matter if something is opt-out quadruple opt-in. Users think of spam as “email I don’t want,” not “email I didn’t sign up for.”  As Stephanie says, bad email I signed up for is even worse than unsolicited email in some ways.  And look at the other side of the argument as well:  would you really mind getting an unsolicited/unpermissioned email if the content or offer was highly relevant to you, e.g., you seriously consider clicking through on it?

2. Permission can be easily faked or loopholed. Companies can operate multiple web sites and email lists and gather addresses from multiple sources and then point to the one “proper permission site” and claim that’s the origin of all the names on its list.  And companies can set up privacy policies in such a way that they can automatically opt users into multiple lists without the user’s permission unless the user reads the fine print.

3. Permission is hard to measure. Besides the fact that permission can be faked, the main way that blacklists and filters try to measure permission is by looking at spam trap hits.  Sometimes this works — the cases where the spam trap addresses are newly-created addresses that never sign up for lists.  But most ISP and other spam trap networks also include recycled email addresses as well — addresses that were real and probably did sign up for email newsletters and marketing at one point but have since gone inactive.  Yes, a mailer that hits this kind of spam trap address is probably guilty of sloppy list hygiene and poor or nonexistent targeting and customer segmentation.  But does this mean they’re a truly egregious spammer?

4. Reputation trumps permission. The world of reputation systems is driving quickly to the point where we can tell much more accurately and automatically if a mail stream is “good” or “bad” as defined by users in terms of complaints and as defined by infrastructure security, authentication, and various other metrics.

So where I come out on this is that permission is FAR LESS RELEVANT than it used to be for receivers as filtering criteria, but probably not 100% irrelevant yet.  Perhaps in a couple years as reputation data-driven filtering becomes refined and the norm, we will be able to be more accepting of highly targeted and relevant unsolicited email (as we are sometimes with highly targeted and relevant postal mail), but I’m not sure the world is psychologically there just yet.  There’s still too much egregious spam in the inbox, and as a result, while users primarily think of spam as “email I don’t want,” they also do still think of spam as “email I didn’t ask for.”

But for now, senders can certainly rely on permission — if and only if it’s up to date and contextual — as “first pass” screen on relevancy.

Where do you come out on this?

(This is the second post in the series…….the first one on When to Hire your First Chief Revenue Officer is here.)

If you’re looking for a great CRO, one thing you want to avoid is being “sold” by a dynamic and engaging salesperson instead of finding the best CRO for your company. Over the two-plus decades of working closely with CROs I figured out what “great” looks like and I’ve found that there are five things that great CROs do. While you might not find all these characteristics and attributes in one person, you should definitely look for them!

First, a great CRO knows when to turn up the volume, and when not to.  Thinking through our metaphor/framework for enterprise sales that I wrote about in an earlier post – from Whiteboard to Powerpoint to PDF – great CROs know when they aren’t yet in PDF mode.  In the early days when your organization is selling on Whiteboard or figuring out the transition to Powerpoint, when you’re adding sales reps like crazy, this is not the time to quickly get to the PDF stage even though everyone in your organization will be clamoring for that. Sure, there could be a ton of opportunity to pursue but scaling quickly is inefficient and unlikely to be successful because scaling before the PDF stage still depends on the success of individual hunters.  Only when the organization has made the true transition to PDF can a sales machine scale rapidly, and a great CRO understands this.

Second, a great CRO gives credit to others first when things go well and looks inward first when things go poorly.  This is easier said than done because the tendency for people in any organization is self-preservation and the easiest way to do this is take credit and blame others. But the geat CROs are the first ones to thank their fellow executives in marketing, in product, in finance, for collaboration and successes.  They are also the first ones to thank their team publicly for a good quarter.  When they miss a quarter, the first thing they do is figure out why the Sales team blew it, as opposed to blaming the product or marketing or economy…or even customers themselves.

Third, a great CRO is maniacally focused on building a conveyor belt-style pipeline for sales talent so they don’t lose momentum when a rep quits or gets fired.  Notice that I didn’t say a great CRO was “focused” on building the pipeline or “passionate” about building the pipeline—I used the term “maniacal” because that’s what a great CRO looks like to everyone else in the organization: a crazy, intense, nonstop, extremist who religiously works on their talent pipeline.  “Quota just walked out the door” is never something you’ll hear from a great CRO because that’s not an option in a well-tuned sales machine where multiple layers of reps are consistently trained, managed, and groomed for the next level of selling. 

Fourth, a great CRO will be able to say “no” to overpaying and over-promoting without ruffling feathers on the sales team. An inability to stay disciplined on compensation is the second-worst thing a Sales leader can do and if they get compensation wrong by paying reps too much base or having too much commission in easily-repeatable form, you’ll pay for it—without the producivity gains. Reps who are overpaid get “fat and happy,” when what you want is for them to be “lean and hungry.” The worst thing a CRO can do? The worst thing a CRO can do, and something the great CROs won’t do despite great pressure, is to promote a superstar sales rep with no management aptitude or training into a sales manager role. I’ve seen this play out several times and it doesn’t end well. Either the superstar will not be able to lead and will exit the organization, or the superstar will end up poisoning an entire team and lots of your reps will exit the organization.  Great CROs know how to say no to the misguided request for a promotion and how to keep people engaged without overpaying them.

Fifth, a great CRO deosn’t belive in the “magic rolodex” (yes, I realize that term is a bit dated!). They might have a magic rolodex, deep networks, and personal ties to players in the ecosystem, but unless you are hiring a sales rep who literally just finished selling a competitive solution to the same target customer set, sales reps who claim they come with a built-in book of business can only deliver on that promise 1% of the time.  It’s alluring — but it just doesn’t work out that way.  Great CROs know how to ferret that out and hire instead the reps who will fit in the company culture and work to improve the processes and systems in place.

Hiring a great CRO isn’t easy but hiring the first (or last) person you interview because of their excellent communication skills will be a disaster. Look for a CRO who understands the pacing to scaling, is humble enough to give credit to others and avoid blaming, and who is “maniacal” about the team—coaching and mentoring them, providing the rails so that the team can do their best work.

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