Another United Odyssey

Despite being (or perhaps, because of being) a 2 million mile lifetime flyer on United, I generally do my best to try and avoid them.  But once in while, routes being routes, I decided to give them a chance and see if things have improved.

Silly me.

Today’s odyssey begins in Hartford where what looked like a fairly empty flight (from the check-in seatmap) ends up an overbooked mess at 6:30 AM.  The weather in Chicago chips in for some fun and after boarding 25% of the plane, they stop, and ask us to de-board citing a ground stoppage in Chicago.

Being one of the first on the plane I am one of the last off and face this line for a cup of coffee at Dunkins. (You can see the sign way down at the end.)


We’re not off to a good start.  About 30 minutes later,  and before I could finish my hard-earned cup of Joe, we board again.  I am constantly using my United app to decide on the likelihood of making my connection.  But the whole time we’re boarding it shows us arriving at 845 and my flight leaving at 910.  Until they close the door.  Now it says 930 arrival, which quickly turned into 950.  Unless my connection is delayed, too — I am toast.  (And the app has let me know is that my flight had already landed from Hawaii hours before and ergo wasn’t going to get badly outbound delayed, due a late in-bound at least.)

So, now, I’m screwed.  If they had just been honest and either told me (or given me the information to conclude) that I had 0% of making my connection, I would have gotten off the plane.  I needed to back on the East Coast later that week and knowing that Chicago is in trouble and San Francisco is also having bad weather, I knew I would be toast if I showed up in Chicago connection-less.

Part of the problem here is misinformation — when my outbound showed no delay, United’s staff response was “they always show no delay right up until they delay it” — which gave me some hope that the outbound would be subsequently delayed and kept me on the plane.

Well, connection-less in Chicago is exactly what happened, after my outbound was delayed twice so I managed to miss it, just two gates down, by about 10 minutes.  Thanks for waiting.

Then I look at the customer service line, which was literally as long as a football field.  (You can’t even see the end of this one.)


I don’t think I’ve seen a line that long (and that’s before even entering the roped back-and-forth real line on the right) in a decade.

I slip into the United Club (which for some reason I still pay for) and it resembles a refugee camp at this point.  I fire up my web browser to look at rebookings.  I quickly realize — and this is possibly a good thing — that the United mobile app has way more functionality in this situation than the website which — and this is a bad thing — is basically useless and tells me I need to call and rebook.

I use the United mobile app.

The trick is every flight is full / standby, but one.  So I choose that one, for a whopping 10 hour delay in arrival.  Since I had ponied up for a First Class seat, I figured it would only show me flights with First available.  Nope.  They put me into an economy middle seat on a First Class fare without saying anything, proposing a refund, nothing.  Not a peep.

This continues United’s tradition of basically ignoring whether you paid extra for Economy Plus (where they are so careful to price each seat) or even First Class when things go awry.  All that’s out the window.

I figure First is small so maybe it’s unavoidable.  And then I see that they have been upgrading people into First on earlier flights that I am standby on instead of giving me the ticket that I paid for.  I look at my place on the “complimentary First Class upgrade” line for the flight they have me on standby — and I’m number 36.  But wait, I’m not asking for a complimentary upgrade.  I paid nearly $1000 for a one-way ticket that I needed to buy on short notice.

No one cares.  United Twitter support which promptly offers to help when I first reported my troubles goes silent when I raise this issue.  You feel a mentality of, “whatever, it’s a crisis — you should be happy with any seat regardless of whether we chose to charge you a premium when you bought it.”  I beg to differ.  If you want me to not care at crisis time, don’t care at purchase time.

Then I notice that the 777 is configured 3-4-3 in coach.  The 777 was designed to 2-5-2 but in order to squeeze in an extra seat per row, ever customer-centric United has decided to go 3-4-3 on some models, and of course this is one.

The hits just keep coming.  Everything they do to reduce my experience they have done.

I call my wife and she says to try another airline.  “No, that won’t work,” I say.  “The weather’s the problem and I’m sure if seats were available on other airlines, United would be routing people to them — instead of making them 12 hours late.  I’m sure that every flight on every airline is toast.”

Amazingly, I still give too much credit to United and too little to my wife. About 4 clicks later, I have a bulkhead seat on American.

I arrive 6 hours late having traveled 16 hours door-to-door on an East Coast flight and having needed to purchase a pricey second ticket on American.

The moral is to avoid two things at all costs:  one-stop travel (I should have driven the extra hour to Boston) and United.

Aligned to Achieve: A B2B Marketing Classic

Tracy Eiler and Andrea Austin’s Aligned to Achieve came out today and it’s a great book on an important and all too often overlooked topic:  how to align sales and marketing.

I’m adding it to my modern SaaS executive must-read book list, which is now:

So, what do I like about Aligned to Achieve?

The book puts a dead moose issue squarely on the table:  sales and marketing are not aligned in too many organizations.  The book does a great job of showing some examples of what misalignment looks like.  My favorites were the one where the sales VP wouldn’t shake the new CMO’s hand (“you’ll be gone soon, no need to get to know you”) and the one where sales waived off marketing from touching any opportunities once they got in the pipeline.  Ouch.  #TrustFail.

Aligned to Achieve makes great statements like this one:  “We believe that pipeline is absolutely the most important metric for sales and marketing alignment, and that’s a major cultural shift for most companies.”  Boom, nothing more to say about that.

The book includes fun charts like the one below.  I’ve always loved tension-surveys where you ask two sides for a view on the same issue and show the gap – and this gap’s a doozy.

sm gap

Aligned to Achieve includes the word “transparency” twenty times.  Transparency is required in the culture, in collaboration, in definitions, in planning, in the reasons for plans, in process and metrics, in data, in assessing results, in engaging customers, and in objectives and performance against them.  Communication is the lubricant in the sales/marketing relationship and transparency the key ingredient.

The book includes a nice chapter on the leadership traits required to work in the aligned environment:  collaborative, transparent, analytical, tech savvy, customer focused, and inspirational.  Having been a CMO fifteen years ago, I’d say that transparent, analytical, and tech savvy and now more important than ever before.

Aligned to Achieve includes a derivative of my favorite mantra (marketing exists to make sales easier) in the form of:

Sales can’t do it alone and marketing exists to make sales easier

The back half of that mantra (which I borrowed from CTP co-founder Chris Greendale) served me well in my combined 12 years as a CMO.  I love the insertion of the front half, which is now more true than ever:  sales has never been more codependent with marketing.

The book includes a fun, practical suggestion to have a bi-monthly “smarketing” meeting which brings sales and marketing together to discuss:

  • The rolling six-week marketing campaign calendar
  • Detailed review of the most recently completed campaigns
  • Update on immediately pending campaigns
  • Bigger picture items (e.g., upcoming events that impact sales and/or marketing)
  • Open discussion and brainstorming to cover challenges and process hiccups

Such meetings are a great idea.

Back in the day when Tracy and I worked together at Business Objects, I always loved Tracy’s habit of “crashing” meetings.  She was so committed to sales and marketing alignment – even back then – that if sales were having an important meeting, invited or not, she’d just show up.  (It always reminded me of the Woody Allen quote, 80% of success is showing up.)  In her aligned organization today, the CEO makes sure she doesn’t have to do that, but by hook or by crook the sales/marketing discussion must happen.

Aligned to Achieve has a nice discussion of the good old sales velocity model which, like my Four Levers of SaaS, is a good way to think about and simplify a business and the levers that drive it.

Unsurprisingly, for a book co-authored by the CMO of a company that sells market data and insights, Aligned to Achieve includes a healthy chapter on the importance of data, including a marketing-adapted version of the DIKW pyramid featuring data, insights, and connections as the three layers.  The nice part is that the chapter remains objective and factual – it doesn’t devolve into an infomercial by any means.

The book moves on to discuss the CIO’s role in a sales/marketing-aligned organization and provides a chapter reviewing the results of a survey of 1000 sales and marketing professionals on alignment, uncovering common sources of misalignment and some of the practices used by sales/marketing alignment leaders.

Aligned to Achieve ends with a series of 7 alignment-related predictions which I won’t scoop here.  I will say that #4 (“academia catches up”) and #6 (“account-based everything is a top priority”) are my two favorites.

Congratulations to my long-time friend and colleague Tracy Eiler on co-authoring the book and to her colleague Andrea Austin.

The Era of Consumer Deception:  Why Do We Tolerate Such Price Opacity?

I was wondering the other day why Southwest would spend millions of dollars to remind people that Bags Fly Free.  I’d argue there are two reasons:

  • It generally supports their friendly and transparent, low fees brand strategy
  • It reminds customers that a $500 fare on United might actually cost you more than a $550 on Southwest if you’ve got a few bags

Price have become so opaque over the past few decades that not only are consumers routinely surprised when they receive a bill, but companies now feel compelled to spend millions to remind them that quoted prices are often apples/oranges comparisons.

It’s not hard to find examples of price opacity:

  • Mortgages with variable rate structures people don’t understand and which exposes them to massive increase in payments (i.e., the 2008 crisis).
  • Bank accounts that have no monthly fee, but are laden with subtle and not-inexpensive fees that seem to silently sneak back in as terms are quietly changed.
  • Numerous airline refundability tiers, change fee policies, per-seat premium economy seat fees, and baggage fees that make true price comparison next to impossible.
  • Rental car policies like Hertz’s usurious $10/gallon refueling fee or the maze of overpriced and often unneeded insurance options that can double the price of a rental
  • Teaser rates for many services, including cellular and Internet, that bear no resemblance to the actual monthly fees

Most, but not all, of the time I manage to sidestep these problems because I’m sophisticated and can figure them out (when I take the time), because I carry balances that preclude most of the sneaky banking fees, and because I fly a lot and get exempt from some of the change fees and seat fees.

But just the other day, while I was in the midst of congratulating myself for avoiding the Hertz $10/gallon refueling fee, I looked on the receipt and saw a per-mile fee that nearly doubled the cost of my rental — when was the last time a rental car didn’t have unlimited miles?

It’s a cat-and-mouse game and companies keep getting better at playing it.

Now you could argue that this opacity is a company’s way of fighting back against price competition, and particularly the price transparency and comparability that the Internet brought.  In an era of price comparison engines that scour the Internet for the best deal, why not sneak in some fees that give you an edge?

You can argue, as people often do when it comes to the airlines, that we’ve done it to ourselves – our consumer behavior has trained the companies towards these strategies.  And that may be true, but we need to accept that these strategies are often fundamentally dishonest.

I realized this as my kids got older and I had to explain how rental cars work (which I still don’t know that well apparently), how airfares work (self-insure against cancellation by throwing out a ticket every now and then as opposed to getting gouged on refundable fares – or just fly SouthWest), how credit cards work (that’s a long one), how mortgages work, and on and on.

It’s what in Texas they call a boiled frog problem. It’s happened so slowly and incrementally that we’ve just gotten accustomed to it and the people most hurt by the practices tend to be at the bottom of the socioeconomic ladder (e.g., payday loans) and have the least voice.

And this society of deception already extends well beyond consumer pricing.  Contests and prizes are another huge area, like fake $1M TV show prizes (e.g., America’s Got Talent) that are actually a 40-year annuity worth more like $300K, fake unwinnable TV contests like American Ninja Warrior (which has only been completed twice) which are made harder every year so nobody wins the fake 40-year $1M annuity, or even state lotteries (which started the annuity deception) which typically pay out over 20 years, slashing prize values by about half.

But where we’ve ended up is not acceptable.  Ironically, after the Internet brought a brief wave of price transparency, we have ended with potentially more opacity than we had before as fees and terms and packaging get ever more complex.  We’re eroding consumer trust by living in an era of manufactured confusion and price deception.

You may not think this is a big deal, but I’d argue it’s like Malcom Gladwell’s broken window theory.  If we tolerate constant small deceptions in our lives, we open the doors to the big ones.

Thoughts on the Coupa S-1

It’s been a while since I dove into an S-1 and while I almost never get all the way through, here we go with another quick romp through a recent S-1.

Coupa, a ten-year old company that sells cloud-based spend management software and who pitches “value as a service” (ugh) recently filed its S-1.  Before diving in, I wonder if I should mention the potential irony in a company that sells “spend management” software running with a 40% operating loss.

But, remember the average SaaS business, per research from my friends at JMP, has negative operating margins at IPO time:  the median is -21% and the mean -36%.   So cheap jabs aside, Coupa is running a bit on the high side and, more importantly, in a time where I thought the markets were demanding better profitability than in the past.  That’s the interesting part.  From an operating margin perspective, Coupa is looking like a typical IPO in a market that was supposedly setting a higher bar.

Coupa’s most recent $80M private round put it in unicorn status (i.e., meaning that it was raised at a $1B+ valuation).

Estimating the shares outstanding after the offering is frankly quite confusing (e.g., share counts in the summary P&L seem to not include conversion of the preferred) and after spending 20 minutes trying to figure this out, I think there will be something like 180M shares outstanding after the offering.

Normally that might suggest a reverse split prior to IPO (as Talend recently did, an eight-for-one) but since I can’t find any evidence to suggest that, I’ll have to assume that Coupa and its bankers are bullish on valuation.  Otherwise, if I’ve got the right share count, any valuation less than about $1.8B will put them in single-digit stock price territory (which is the condition companies do reverse splits to avoid).

Highlights from the first pages of the S-1:

  • They connect 460 organizations (customers) with over 2M suppliers, globally
  • They estimate they have saved their customers $8B to date, on a cumulative basis
  • Fiscal year (FY) ends 1/31
  • FY15 revenues of $50.8M, FY16 of $83.7M, 65% YoY growth
  • FY15 net losses of $27.3M, FY16 of $46.2M, 68% YoY growth
  • 1H16 revenues of $34.5M, 1H17 of $60.3M, 75% YoY growth – accelerating

Now, let’s look at the income statement, which I’ve cleaned up and color-highlighted.


Income statement comments:

  • Approximately 90%/10% mix of subscription to services, generally good
  • $83.7M revenues in last full FY is appropriate IPO scale by recent historical standards
  • 75% accelerating YoY growth in 1H17 over 1H16 is pretty strong
  • Subscription gross margins running 77% to 80%, pretty standard
  • Services gross margins of -89% in FY16 and -59% in 1H17 are horrific.  Happily it’s only 10% of the business.
  • Overall gross margins run around 60%, which strikes me as a bit low, but according to my JMP data, is roughly on target
  • 1H17 R&D of 25% of revenues, at the mean
  • 1H17 S&M of 58% of revenues, 7% above the mean
  • 1H17 G&A of 17%, 4% below the mean – but after running at a shocking 32% in 1H16
  • 1H17 total opex of 100% of revenues, about 3% above the mean
  • 1H17 operating margin of -39%, about 3% below the mean

They also present a non-GAAP operating loss which I can’t easily benchmark. They define it as:  operating loss before stock-based compensation, litigation-related costs and amortization of acquired intangible assets.  There was about a $12.9M delta between GAAP and non-GAAP operating income in FY16, which reduces to only $3.8M in 1H17.

Back to highlights from the S-1 body copy:

  • They typically do 3-year contracts
  • They say “we rely heavily on Amazon Web Services (AWS)” as a risk in the risk factors
  • 29% of revenues from international in 1H17
  • They had a “material weakness” in their FY14 audit, unusual
  • 25 pages of risk factors in total, normal
  • They’ve raised $165M in venture capital, and have $80M in cash
  • Almost $7M in litigation costs in FY15
  • They claim an estimated LTV/CAC that exceeds 6.0 in each of the past 3 years
  • They do an interesting analysis of their 2013 customer cohort concluding that its contribution margin was -249% in FY13, but 75% in FY14-16. (Page 53.)
  • Average ARR/customer up from $138K in FY15 to $183K in FY16

Here are the quarterly numbers; things look pretty consistent except for 2QF15, where among other things, they had $7.5M in stock-based compensation expense.


More highlights

  • Operating cash burn of about $4M/quarter (page 67)
  • The CEO made $660K in cash comp in FY16, $320K and $340K bonus
  • The EVP of sales made $497K in cash comp in F16, $250K base and $247K commissions

Let’s take a closer look at the unicorn round:

  • It raised $80M at $4.18/share (page 119)
  • The beneficial ownership analysis (page 121) is based on 162.8M shares outstanding as of 7/31/16, but I believe excludes 61M shares associated with granted and un-granted stock options (page 43)
  • 162.8M + 61M = 223.8M shares on a fully diluted basis x $4.18/share = $935M
  • Not a unicorn you cry! ($935M < $1B)
  • But remember these claims are usually based on post-money valuation
  • $935M + 80M = $1.015B
  • So the math appears to hold up, but it’s also pretty clear Coupa was holding out for a valuation that squeaked them into the club

# # #

Be sure to read my disclaimers.

Win Them Alone, Lose Them Together

It was back in the 1990s, at Versant, when my old (and dearly departed) friend Larry Pulkownik first introduced me to the phrase:

Win Them Alone, Lose Them Together

And its corollary:

Ask for Help at the First Sign of Trouble

Larry told me this rule from the sales perspective:

“Look, if you’re working on a deal and it starts to go south, you need to get everyone involved in working on it.  First, that puts maximum resources on winning the deal and if — despite that effort — you end up losing, you want people saying ‘We lost the Acme deal,’ not ‘You lost the Acme deal.'”

It’s a great rule.  Why?  Because it’s simple, it engages the team on winning, and most of all — it combats what seems to be a natural tendency to hide bad news.  Bad news, like sushi, does not age well.

Twenty years later, and now as CEO, I still love the rule — especially the part about “the first sign of trouble.”  If followed, this eliminates the tendency to go into denial about bad news.

  • Yes, they’re not calling me back when they said they would, but I’m sure it’s no problem.
  • They did say they expected to be in legal now on the original timeline, but I’m sure the process is just delayed.
  • Yes, I know our sponsor seemed to have flipped on us in the last meeting, but I’m sure she was just having a bad day.
  • Well I’m surprised to hear our competitor just met with the CIO because they told us that the CIO wasn’t involved in the decision.
  • While the RFP does appear to have been written by our competitor, that’s probably just coincidence.

These things — all of them — are bad news.  Because many people’s first reaction to bad news is denial, the great thing about the “first sign” rule is that you remove discretion from the equation. We don’t want you to wait until you are sure there is trouble — then it’s probably too late.  We want you to ask for help at the first sign.

The rule doesn’t just apply to sales.  The same principle applies to pretty much everything:

  • Strategic partnerships (e.g., “they’ve gone quiet”)
  • Analyst relations (e.g., “it feels like the agenda is set for enemy A”)
  • Product development (e.g., “I’m worried we’ve badly over-scoped this”)
  • Financing (e.g., “they’re not calling back after the partner meeting”)
  • Recruiting (e.g., “the top candidate seemed to be leaning back”)
  • HR (e.g., “our top salesperson hated the new comp plan”)

I’ll always thank Larry for sharing this nugget of wisdom (and many others) with me, and I’ll always advise every manager I know to follow it.

The Four Levers of SaaS

There are a lot of SaaS posts out there with some pretty fancy math in them.  I’m a math guy, so I like to geek on SaaS metrics myself.  But, in the heat of battle running a SaaS company, sometimes you just need to keep it simple.

Here’s the picture I keep on my wall to help me do that.

It reminds me that new ARR in any given period is the product of four levers.

  • The MQL to stage 2 opportunity conversion rate (MTS2CR), the rate at which MQLs convert to stage 2, or sales-accepted, opportunities.  Typically they pass through a stage 1 phase first when a sales development rep (SDR) believes there is a real opportunity, but a salesperson has not yet agreed.
  • The stage 2 to close rate (S2TCR), the rate at which stage 2 opportunities close into deals, and avoid being lost to a competitor or derailed (e.g., having the evaluation project cancelled).
  • The annual recurring revenue average sales price (ARR ASP), the average deal size, expressed in ARR.

That’s it.  Those four levers will predict your quarterly new ARR every time.

Aside:  before diving into each of the four levers, let me note that sales velocity is omitted from this model.  That keeps it simple, but it does overlook a potentially important lever.  So if you think you have a sales velocity (i.e., sales cycle length) problem, go look at a different model that includes this lever and suggests ways to decrease it.

So now that we have identified the four levers, let’s focus on what we can do about them in order to increase our quarterly new ARR.

Marketing Qualified Leads (MQLs)

Getting MQLs is the domain of marketing, which should be constantly measuring the cost effectiveness of various marketing programs in terms of generating MQLs (cost/MQL).  This isn’t easy because most leads will require numerous touches over time in order to graduate to MQL status, but marketing needs to stay atop that complexity (e.g., by assigning credits to various programs as MQL-threshold points accumulate).

The best marketers understand the demand is variable and have designed their programs mix so they can scale spending quickly in response to increased needs.  Nothing is worse than an MQL shortage and a marketing department that’s not ready to spend incremental money to address it.

The general rule is to constantly A/B test your programs and nurture streams and do more of what’s working and less of what isn’t.

MQL to Stage 2 Opportunity Conversion Rate

Increasing the MQL to stage 2 opportunity conversion rate (MTS2CR) requires either generating better MQLs or doing a better job handling them so that they convert into stage 2 opportunities.

Generating better MQLs can be accomplished by analyzing past programs to determine which generated the best-converting MQLs and increasing them, putting a higher gate on what you pass over to sales (using predictive or behavioral scoring), or using buyer personas to optimize what you say to buyers, when, and through which channels.

Do a better job handling your existing MQLs comes down ensuring your operational processes work and you don’t let leads fall between the cracks.  Basic activity and aging reports are a start.  Establishing a formal service-level agreement between sales and marketing is a common next step.

Moving up a level and checking that your whole process fits well with the customer’s buying journey is also key.  While each step of your process might individually make sense, when assembled the process may not — e.g., are you irritating customers by triple-qualifying them with an SDR, a salesrep, and a solution consultant each doing basic discovery?

The Stage 2 to Close Rate

Once created, one of three things can happen to a stage 2 opportunity:  you can win it, you can lose it, or it can derail (i.e., anything else, such as project cancellation or “slips” to the distant future).

Increasing your win rate can be accomplished through better product positioning, sales tools, and sales training, improved competitive intelligence, improved buzz/aura, improved case studies and customer references, and better pricing and discounting strategy.  That’s not to mention more strategic approaches via improved sales methodology and process or product improvements, in terms of functionality, non-functional requirements, and product design.

Decreasing your loss rate can be accomplished through better up-front sales qualification, better sales tools and training, improved competitive strategy and tactics, and better pricing and discounting.  Improved sales management can also play a key role in catching in-trouble deals early and escalating to get the necessary resources deployed to win.

Reducing your derail rate is hard because project slips or cancellations seem mostly out of your control.  What’s the best way to reduce your derail rate?  Focus on velocity — take deals off the table before the company has a chance to prioritize another project, do a reorganization, or hire a new executive that kills it.  The longer a deal hangs around, the more likely something bad happens to it.  As the adage goes, time kills all deals.


The easiest way to increase ARR ASP is to not shrink it through last-minute discounting.  Adopt a formal discount policy with approvals so that, in the words of one famous sales leader, “your rep is more afraid of his/her sales manager than the customer” when it comes to speaking about discounts.

Selling value and product differentiation are two other discount reduction strategies.  The more customers see real value and a concrete return for their business the less they will focus on price.  Additionally, the more they see your offering as unique, the less price pressure you will face from the competition.  Conversely, the more they see your product as a cost and your company as one of several suppliers from whom they can buy the same capabilities, the more discount pressure you will face.

Up-selling to a higher edition or cross selling (“fries with your burger?”) are both ways to increase your ASP as well.  Just be careful to avoid customers feeling nickled and dimed in the process.

For SaaS businesses, remember that multi-year deals typically do not help your ARR ASP (though, if prepaid, they do help with year-one cash).  In fact, it’s usually the opposite — a small ARR discount is typically traded for the multi-year commitment.  My general rule of thumb is to offer a multi-year discount that’s less than your churn rate and everybody wins.


Hopefully this framework will make it easier for you to diagnose and act upon the problems that can impede achieving your company’s new ARR goals.  Always remember that any new ARR problem can be broken down into some combination of an MQL problem, an MQL to stage 2 conversion rate problem, a stage 2 to close rate problem, or an average sales price problem.  By focusing on these four levers, you should be able to optimize the productivity of your SaaS sales model.



On Hiring: Promote Stars, Not Strangers

“Well, he’s never been a sales development rep (SDR) manager before, but he has been an SDR for 3 years at another company. The chance to be a manager is why he’d come here.” — Famous Last Words

I can’t tell you the number of times I’ve heard something akin to the above in hiring processes.

Of course he’d come here to get the chance to be a manager.  The question is why his current employer won’t make him one?  They’re the ones who know him.  They’re the ones who’ve worked with him for three years.  What do they know that we don’t?

As a general rule, startups are not the place to learn how to do your job.  At startups, you should hire people who already know how to do the job.  Running the startup, in a high-growth, frenetic environment, is hard enough; you don’t need to be learning how to do your job at the same time.  A key reason startups offer stock options is precisely this:  to incent people who already know how to do the job to do it again by participating in the upside.

This is not to say, reductio ad absurdum, that startups should have no entry-level jobs, never take a bet on inexperienced people, and never promote anyone into management.  That’s a recipe for losing your best people when they decide the company has no interest in their personal development or career path.  The best startup teams are a mix of veterans and up-and-comers, but since — particular for management hires — you need to have a mix, you need to be very careful to whom you give that first-time in-the-job slot.

This is why I made the Star/Stranger Promotion Quadrant.

star promotion

The two axes are simple:  is the person a known star (at this company, i.e., do we all known her and do we all think she’s a star, here) and has the person done the job before (i.e., the actual job, SDR manager in this case, not SDR).

One of the easiest things you can do is to appoint known stars.  This means the person works today at your company in a different role, but wants to do a new job that’s opened up, and has already done that exact job before.  It doesn’t happen that often, but sometimes your director of product management has been director of product marketing before and wants to get back to it.  Awesome.  I call this “appointing” known stars because while the move may involve a titular promotion, in reality it’s more of an appointment than a promotion.  It’s great to let people move around the organization and there should be no shame in ever wanting to move back to something that someone particularly likes doing (or that the company really needs).  I shade this green because it’s low risk.

One of the nicest things you can do is to promote known stars.  For example, take a top-performing SDR who has management potential (an elusive concept, I know, but a whole post unto itself) and give them the chance to run a piece of the SDR team.  I prefer to do this — especially for first-time promotions into management — on a reversible basis.  Since neither side is certain it’s going to work, I believe it’s best to make someone a “team lead” for six months and then assess how it’s going.  If it’s going great, promote them to SDR manager and give them a raise.  If it’s not going well, you haven’t burned the ships on making the person a regular SDR again, working on some skills, and trying again in the future.  I shade this purple because there is some risk involved, but it’s a good risk to take.  People in the organization want see others given the chance to succeed as well as to safely fail in taking on new challenges.

If you lack existing team members with management potential or if your current team has too many first-time (and too few experienced) managers, then your best move is to hire qualified strangers.  While the stranger might want a career step-up, the reality is that most companies hire new people to do jobs they already know how to do.  Cross-company promotions are rare and candidates offered them should be somewhat wary.  Why again are these people willing to make me a CMO for the first time?  Sometimes the reasons are good — e.g., you’ve been a divisional marketing VP at a larger company and move into a startup.  Sometimes the reasons are bad.  Think: why won’t any qualified CMO (who knows this space) take this job?  But, moving back to the employer perspective, I shade this square purple because external hiring is always risky, but you can minimize that risk by hiring people who have done the job before.

This takes us back to the start of this post.  While depending on the kindness of strangers may have worked for Blanche Dubois, as a hiring manager you should not be extending such kindness.  Hiring qualified people is risky enough.  New hires fail all the time — even when they are well qualified for job with lots of relevant prior experience.  Don’t compound the risks of cultural fit, managerial relations, attitude/urgency, and a hundred other soft factors with the risk of not knowing how to do the job in question.  What’s more, do you have time to teach one of your managers to do their job?  Especially when what’s needed is teaching in basic management?  As I often say, VCs are risk isolators more than risk takers, and hiring managers should think the same way.  That’s why you should almost never promote strangers.  (And, as a corollary why strangers should be wary of those willing to promote them.)

That’s why I’ve colored this square red.  Companies should hire outsiders to do jobs that candidates already know how to do.  Promotions are reserved for promising insiders.

Put differently, and from a career planning viewpoint:  “rise up, jump across.”