Missing Your Market? It’s Not Always About Sales Skills. Sometimes It’s About “Fit”


Sometimes, it’s just about “fit.”

It’s not how sharp you are, or how well you can sell.

It’s not about your prospecting chops, or how you present.

It can just be that you miss the mark…with the market.

Or as Johnny Cochrane famously said…

(thank you, giphy)

What does this mean?

That maybe you have a great offer…but the wrong market.

Or that your market moved.

Or that your “motion” (or approach) to the market doesn’t align with the size and needs of the market.

Any of these sound like they might be your challenge?

At least 4 times in my career, I’ve seen businesses “miss” something major in the market.

When that happens, sales effort doesn’t decline as the business tries to grow.

It’s just as challenging to win each subsequent customer.

A business SHOULD find it easier to drive new business as it’s established. The cost to find and “buy” a customer should fall over time as the business matures and gains a foothold in a market.

Each customer should make each subsequent customer easier to win, and less expensive.

When that’s not the case, that means something’s off…it’s not working as it should.

I’ll walk you through a few examples so you can determine if any of these may be the clog in your sales pipe.

(thank you again, tenor)


Mismatch 1: The Market Moved


In the late twenties, I worked with a voluntary benefits brokerage. The company had been built by offering company-endorsed auto and home insurance to large employers.

And by large, I am talking about 25,000+ employees.

They’d started in the late 90s, gotten ahead of a lot of competitors in the space, and built a nice, recurring stream of cash flow.

Over the next 15 years, they added other products to sell to those large customers, from supplemental insurance (accident, hospital, disability, long-term care, etc…) to consumer products.

But then competition took notice of the commissions on these products. And started saying, “Hey, give US that business…”

The competition was much bigger, much better funded, and had relationships with more senior execs.

So the competition – think Lockton, Marsh, etc… – could pick off the best customers by offering something smaller players couldn’t compete with. Discounts on major medical insurance consulting, and more.

Customers are effectively trained over time by vendors, and these vendors train customers to want a one-stop shop (plus “discounts”).

That little business couldn’t compete with the major brokerages anymore. The big potential customers weren’t interested in a niche player.

(thank you, tenor)

The market effectively “moved” on.

And so this little business had to find a new way to compete.

The best answer for that company? Sell to someone who had a strategic advantage.

In your situation, has your customer base – or a segment of it – moved on to a different solution? Different pricing models? A different need?

If so, is focusing on better sales the best answer?

Mismatch 2: The Market Just Isn’t Ready…For That


Recently, I worked with a small professional services provider. Sharp professional who knows her stuff.

She’s got a niche in healthcare, and offers deep expertise in the business of that industry.

She wants – and deserves – to be paid for it.

But there’s a problem.

Her clientele – where she is now – aren’t ready for her pricing.

(thank you, giphy)

They’re startups. But not the “we’ve got series A type money to spend” startups.

They’re more of the “I’m paying for this out of my savings and I don’t know what a financial model is” type.

Paying 5 figures for something they think they can do online isn’t going to work. No matter how much I coach and work on positioning, framing, anchoring and finding reasons to do business.

So she’s stuck. She’s made a name for herself here… but runs into the same problem all the time.

Ever seen this? You’re wanting to charge Ritz Carlton rates for people who want to spend like it’s the Holiday Inn Express?

She has a few options. She can:

  • Work to move upmarket, which will require an investment of time and money to get attention and a pipeline;
  • Drop her pricing to win business in the short term while she does the above; OR
  • Adjust her offer to fit with where they are in the life cycle of their business. That might look like this: a lower up-front rate, with an ongoing monthly service fee for X amount of work, as needed. Over time, these would stack into a nice, consistent stream of cash flows.

Is your market ready TODAY for what you’re selling, and the way you’re selling it?

If not, you’ve got some hard decisions to make.

Mismatch 3: The Market Just Ain’t Big Enough…For Your Approach


Some approaches to sales are really popular. People rave about the results. And it works for so many you might think, “That’s what we need.”

So you give it a shot. And it works.

Until it doesn’t.

Like Boston Consulting Group’s Experience Curve Model… It was great for many, but not everyone.

(thank you, giphy)

An example of this… the 7 Touch System.

This was largely developed by tech companies’ sales teams sometime in the last 15 years. In short, it’s a structured prospecting sequence to a target company. 4 calls, 3 emails and spread out over X number of days.

A lot of people had success with it because it’s something they could do (it’s simple) and measure (because they did it, and it was simple).

But what happens when your market … is limited? To 300 or 700 or 1000 prospects?

(thank you, giphy)

You end up calling the same people over and over… and the question comes up, “What do I say the next time I call them?”

I worked with another insurance brokerage who has a very specific – but limited – customer base. They built a solid base of customers using the 7 touch system.

And then, after about 2 years, they said, “We’ve called and talked to everyone. What do we do now?”

They had to rethink their approach.

Another company – a SaaS provider selling 7 figure ACV (annual contract value) deals – built a great recurring revenue business. Incredibly valuable.

But they, too, had a finite market.

They started with a small team of sellers taking their product to market. Like most startups do.

As they matured, they bought into the, “We need a full SDR team to do this work” mantra, and built out a larger commercial sales team. Full of sales development reps, senior AEs, the whole deal. (Don’t get me started on the problem of having your least experienced sales people doing the hardest, most challenging work in sales.)

They ran the standard playbook, too, with the 7 touch system.

A few years in, they looked up and saw new sales slowing down.

Like the insurance brokerage, they were calling on the same people, repeatedly. Sometimes in the same year.

And didn’t have a way to break through.

For this company, we suggested a longer-term play to get in:

  • Ranking accounts by most to least likely to buy
  • Mapping accounts to identify all the people likely to be involved in a purchase
  • Building a 2-3 year pursuit plan with multiple touch points and multiple stakeholders
  • A team approach to manage the relationships (and mitigate risk)

That may not be right for you.

But as you look at sales efforts, you may ask yourself, “Does our approach match our market? Based on size of the market? Or how do they buy?”

Yes, you may need to look at the team’s ability to execute on any playbook you put in.

And you likely need to look at your sales process.

And how people are managed.

And the skill level of your team.

But don’t discount that you may be trying to run the wrong play into the wrong defense.


Is your sales engine stalling?
Want to explore where and why?

Email me: adam@thenorthwoodgrp.com

Adam Boyd