Mar 4, 2020 8 min read

Hiring Enterprise Sales Teams Ahead of Product/Market Fit

Hiring Enterprise Sales Teams Ahead of Product/Market Fit
Alex Baldwin in "Glengarry Glenross"

A pattern I’ve seen 4 or 5 times seems worth describing, since other folks may be experiencing it: a very early-stage B2B/enterprise company brings on a full sales team before finding product/market fit. Which leads to a spin cycle of frustration and finger-pointing. It’s easy to write this off as a personality or staffing issue (“If only we had stronger product managers… If only our field sales reps were more flexible…”) rather than a structural challenge where both Sales and Product/Engineering are set up for failure. Here’s my gross simplification.

First, let’s recapping the basics of why we hire enterprise sales teams and what they do.  We hire very expensive sales professionals to bring (somewhat) well-defined propositions to prospects in our (validated) target market; to identify and overcome objections with individual prospects/buyers; and then GET THEM TO SIGN. Sales discussions assume the existence of various well-thought-out-and-tested artifacts such as:

  • A specific target audience that shares a well-recognized problem
  • A clear value proposition, backed up by success stories or clear metrics or ROI calculators, that addresses their common problem
  • Enough solution details to answer reasonable follow-on questions
  • A qualification checklist: what 4-6 answers would qualify a prospect in (i.e. we think they should be interested) or qualify them out (i.e. we think this is a bad fit, uphill sale, wrong problem, our tech won’t work there, competitor owns that vertical…)
  • A preliminary support/customer success model, so we know how we’ll help new users deploy and get value from what they bought
  • Somewhat stable product packaging that identifies what a paying customer gets (and doesn’t get) that delivers actual value
  • A starter pricing model with list prices and sensible upsell tiers/features
  • Marketing and selling materials (website, brochureware, white papers) that consistently support the product story, audience, customer value and top competitive knockoffs.

We put salespeople on a short timeline: they live and die in the current quarter. And every good salesperson knows exactly how much of their quota they’ve retired quarter-to-date. (If not, the VP Sales has a helpful weekly pipeline call to refocus them.) Senior salespeople who fail to meet quota are usually shown the door, while those who beat their target get a trip to Fiji or Aruba for President’s Club. Reps who spend their time doing customer journey mapping or deep technical troubleshooting get transferred out of Sales.

So imagine that we have a B2B whiteboard product concept, but with little market validation and weak understanding of actual customers’ detailed needs. We don’t know what alternatives or objections or price sensitivity or integrations we’ll run into. We lack four or five beta users kicking the stuffing out of our proto-product, stumbling through installation and incomplete UI. We’re hypothesizing about mythical prospects and markets. (“Wouldn’t our stuff be great for healthcare analysts?” “This sounds like something Purchasing organizations could use.” “Our secret sauce could help international funds transfer players to track anomalies.” “Elementary school teachers should love us.”)  Speculating about who might be interested if we could just find them, interview them, restate our benefits/features in their industry-specific terms, start a pilot, quantify real value, get an enthusiastic reference, and ink a contract.

We’re thinking… salespeople spend more time with customers than anyone else. So shouldn’t we hire a B2B sales team, send them out to pitch lots of prospects, and bring back the ones who want our stuff? Combine Lean Startup validation with quick revenue?
Here’s why I don’t see that working:

[1] Most new product concepts are at least half wrong, and many are entirely wrong.

young girl face-palming in frustration

Every time I’ve done discovery on a new product concept, I’ve been surprised at what we didn’t know, or misunderstood, or incorrectly borrowed from another segment. Which customer-side problem statements bombed. Whether imagined user pain is actually painful. How industry-specific incentives or regulations shape needs. Which workarounds and substitutes are adequate. When my expert intuition and the executives’ assumptions were off the mark.
Pick your number: HBR claims that 95% of new products fail, and I see whiteboard concepts fail at similar rates, even if they come from executives or founders. Notwithstanding that our team is much smarter than average.

Discovery needs to be fast and iterative and unbiased. Intellectually honest product validation is the search for “NO” as much as for “YES.” The sooner we can knock down one fruitless hypothesis or refine our understanding of customer pain, the sooner we can test our next candidate. I’d much rather spend 6 weeks learning that my pet theory was wrong, than spend a year and $2M turning that pet theory into a finished product. Because building something that doesn’t sell is 100% waste even if beautifully designed and brilliantly engineered. So our bias needs to be toward fast learning and rejecting hypotheses rather than closing early outliers.

[2] We train and reward enterprise salespeople for getting individual accounts to YES. We train and reward product managers for skeptically pattern-matching across markets and large numbers of customers.

Good salespeople are persuasive, persistent, and schooled to turn an individual prospect’s objections into reasons to buy. The goal of a productive sales call is to anticipate shortcomings or problems, have positioned responses ready, and move that specific opportunity through the sales funnel. This is a form of economic combat: our salesperson “wins” by answering objections and getting that singular prospect to YES. Issues are minimized, pushed aside, dealt with quickly, ignored if possible. No salesperson* wants to spend an hour hearing why a missing feature is so crucial, or ask open-ended questions that will raise yet another set of objections.

In contrast, good product managers** doggedly dig into objections, trying to thoroughly understand each one. Because the goal of a validation interview is not to close that specific customer, but to listen for concerns that will come up again and again. To understand root issues and context so that we can solve them later. Product folks want interviewees to share their pain, their workflows, alternative they’ve tried, and the real cost of fixing the problem. (If this customer can’t export CSV files, why not? What have they tried? How much time does it waste? Has their incumbent vendor promised a fix? Why is that export important if we have other ways of pulling data from the system? Have they gone to their manager to demand a solution? Are there other users at this company having the same problem?)
A great outcome is understanding the objection deeply enough to bring back a clear problem description and have the whole development/design team can collaborate on fresh solutions. Or to learn that this user doesn’t care and hasn’t bothered to look for answers.

Especially in the enterprise space, real market validation is painstaking and slower than we want. It’s not easy to schedule. It encourages humility and rewards curiosity. And there’s no guarantee that we ever find a positive answer. Putting discovery on a quarterly clock isn’t helpful.

How Does This Play Out?

When we hire enterprise sales teams too early, we send them out with high-level positioning or vague concepts but without the detailed info and well-crafted artifacts they need to close specific deals. So they work their personal networks for folks who might react well to our high-level proposition. Then they try push for positive buying interest, which inevitably includes lots of customer-side questions about what and how and when and how much and what about.

Fictitious example: our company is building AI-based recruiting software that will spot talent better among stacks of online job applicants. Positioning: “We help drive down the cost of recruiting while filling key openings faster!”  We’ve turned our investor pitch into a 7-slide deck that highlights recruiting costs and millennial hiring trends. It’s silent on target segments, effectiveness, pricing, competitor comparisons, system requirements and ROI because we only have vague guesses so far.

Our Southeast salesperson knows the CHRO of BigPharmaCorp in Atlanta. She comes back from the meeting very enthusiastic, since the CHRO is bonused on recruiting speed and likes our one-line pitch. She’s brought back a short list of reasonable questions, however:

  • When will we be HIPAA compliant?
  • Have we measured our effectiveness on healthcare-specific resumes with heavy scientific or industry terminology?
  • How long will it take to rebuild the presentation with only Pharma terminology, Pharma examples, Pharma images? Can we provide 2 reference accounts in Pharma?
  • Where’s our detailed feature comparison to two pharma-specific recruiting packages?
  • Do we fall under the FDA’s Software as a Medical Device (SaMD) standard?
  • Can we integrate with BigPharmaCorp’s custom-built diversity tracking application?
  • HIMSS, the big healthcare trade show, is in Orlando next week. Will we be exhibiting there?

Meanwhile, our Northeast rep just talked with a colleague at MegaBankNYC and has his finance-specific checklist: support for Know Your Customer regulations, anti-money-laundering reporting, and SOC 2 audit requirements.
And a Federal prospect wants commitments about GSA pricing schedules, ultra-secure on-premise installation options, and project-based custom development through a major DoD contractor.

Follow-up meetings for all three are next week, so our lone product manager abandons work on more systematic validation interviews to rebuild PPTs and knock together imaginary ROIs by vertical market. Because we lack core assets and answers, our three salespeople collectively capture all of Product’s time. And all three deals are likely to flounder on as-yet-unknown technical or economic or organizational problems. (Oops! We’ve already told the Board about our hot new prospects.)

This creates our spin cycle of frustration and finger-pointing. The Sales team is doing its best to find prospects for our untested product concept, hitting internal roadblocks as often as customer-side roadblocks. (From Product: “Our software won’t do that.” “You didn’t ask the right questions.” “Building that special feature would pull our whole team off finishing the core product.” “This customer is an outlier.” From Sales: “Then we need more complete qualification and technical details. These deals were exactly what you asked us for.” “How hard could it be to add those few features?”)

Product supports these proto-opportunities though they are distracting and mostly hopeless. Deep market discovery should our #1 priority, but gets repeatedly postponed as each quixotic deal comes in. It’s easy for each side to take it personally, rather than seeing the underlying problem.

What Do We Do?

Ideally, we wouldn’t find ourselves in this situation. But optimism, urgency and revenue promises to our Board drive us to scale up Sales. What options do we have?

  • I’d start by scaling back Sales to a single senior person until we find our market fit. (Here’s who I’d pick.) At a big company, I’d transfer the remaining team to revenue-generating products.
  • Pair our salesperson with a product manager or UX’er on all discovery calls. And change short-term sales compensation from revenue to successful unpaid trials.
  • Create a structured validation questionnaire with emphasis on problems and alternatives. Give prospects a red marker to “correct” our mocks, presentations, materials.
  • Design a “concierge test” where we do some of the customer’s work and learn what’s missing from our fragmentary offering. (HT: Tristan Kromer.)

None of this will be easy or popular.

Sound Byte

Hiring an expensive sales team to validate product concepts is IMO a colossal mistake. Instead, we need to get our product learning in place and then ramp up a revenue process. Ultimately that will be much cheaper and faster.

* Some salespeople can surely do good product discovery work, just as some finance folks can write website copy and some marketers can debug security protocols. But as a group, salespeople are hired and trained and rewarded and promoted for selling, which is the antithesis of validated learning.

** Discovery is a team effort. I’ve referred here to a solitary product manager, but the best validation interviews include designers and developers/ architects.

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