7 Surprising Sales Lessons I Recently Learned About Scaling to $10M ARR

Scaling a business definitely isn’t for the weak. I’ve spent the past six months overseeing the sales team here at Proposify as we set our sights on our next revenue milestone. And it’s been full of eye-opening, thought-provoking, and sometimes counterintuitive lessons. Here are the things that surprised me most and what I learned from them.

sales lessons learned scaling to 10m arr

12 min. read

I have a confession to make: I have never felt like I know much about sales.

I’ve never worked a sales job once in my life. Outside of door-to-door preaching in my early life, and building two businesses, I’ve never “sold” as a career, or earned a commission cheque.

So it’s not without a healthy dose of irony that I would start a company that makes sales software that we sell to sales leaders.

In the last six months, I’ve overseen the sales team at Proposify, working daily with Daniel Hebert, our Director of Sales. We’ve gone through some ups and a lot of downs moving up-market to target mid-market customers.

It’s been a crash course in sales leadership, and I’ve walked away with several surprising lessons, with hopefully more to share when the time comes.

7 of the most surprising lessons I’ve learned about sales recently

1. Changing markets is a lot like building a new startup from scratch—with one big difference.

One of the biggest mistakes I made so far in business (and I made many) was thinking that moving up-market, building a sales team, and selling to bigger businesses was going to be easy, like layering icing on an already well-baked cake.

In reality, it was more like trying to deconstruct the cake and turn it into muffins without anyone noticing.

It meant realizing customers in the mid-market buy our proposal software for very different reasons than our smaller customers. Our product, positioning and messaging had to change. How we do business changed. It involved unlearning years of ‘the way things are done’ embedded in our company mindset.

Trying to sell a product while building the product is what an early stage startup feels like. It’s laying down train tracks while the train barrels behind us.

In a lot of ways, going from $1 to $10M is much harder than going from $0 to $1M.

What we realized is that the sales team often gets blamed when they aren’t hitting targets, but selling a product that was built for small customers is like selling toques and mittens in Barbados.

Mobilizing a team of three into pivoting markets is a lot easier than mobilizing seventy five people.

We had to start challenging every assumption we had, and dig deep to realign the business to the new customer.

2. Hire the right sales leader for where you are now.

It’s practically in the VC handbook: Startup raises millions in cash, one of the first things they do is get help hiring a seasoned VP Sales from [insert huge SaaS company here] to lead them to high growth.

But go and talk to any CEO, and chances are they’ve fired at least two, sometimes three, VPs.

Why is it so hard?

Because leaders who are great for one company may not be great for another.

Some are shell-shocked when they go from one company with a strong brand and processes in place for the enterprise market where all they need to do is keep the engine humming, to a newer startup where they need to build the engine from scratch.

It’s counter-intuitive, but, when hiring, founders should take their time vetting the right candidate for where they are at right now—not where they want to be.

For example, we once interviewed a candidate for CMO who came from Yahoo! and made $400K a year (about the revenue we made the year prior). It wasn’t a fit on both sides, but I’d argue we’re further ahead now having a less experienced, but more tactical leader.

It can be hard to know when you’re going in the wrong direction but once you have the right leader in the seat, you feel it.

We had spent tens of thousands of dollars over an entire year training our sales team on the Sandler methodology.

Hours every week, across the board, traveling to half-day training sessions. It didn't move the needle. We were frustrated spending all this money with no results.

What had we done wrong? We 'had' a methodology. But we didn't 'implement' a methodology.

Then we hired a Sales Enablement Manager, Daniel Hebert, who had come from multiple startups in Toronto. As soon as he started he started digging into problems and implementing solutions for them one at a time.

So here's what Daniel did:

1. He created decks, scripts, and talk tracks so the reps had guides on how to use the methodology in calls.

2. He installed so we could get visibility into a black box. Was the methodology, the talk track, used? In the right way? He scored the calls.

3. He built custom fields in Salesforce with the key components of the methodology. Reps logged their info directly on opportunities.

4. He used call recordings and methodology fields from our CRM in pipeline reviews, deal coaching, and account maps to help close deals.

Suddenly, bigger and better deals happened. And it didn't take long. Immediate impact within one cycle.

We promoted Daniel to Director of Sales within four months.

After he was promoted he started attacking other problems, like building an outbound playbook, fixing our comp plan, and moving our SDR manager into a sales ops position.

We had fake data in our system that was creating false positives, so he cleaned up outdated opportunities in Salesforce so we could face the cold, hard truth.

Daniel told me to my face every week why things weren’t working, and what we needed to do to solve the issues. No sugarcoating, no smoke blowing. Just harsh truths, and proposed solutions.

Daniel hasn’t been VP at Big Company X. He worked in four B2B SaaS startups, all in early stages, all with few resources, and helped them get to the first $1M+ in revenue. And it shows in his scrappiness and problem-solving abilities.

3. Don’t specialize roles too early.

The common advice is to specialize sales roles, hiring business development reps to go out and find leads, and then account executives to move them through the sales process. Openers and closers.

But doing this too soon when you don’t have a lot figured out can do more harm than good.

When you’re building a product startup you don’t go out and hire one hundred engineers and then say, “Okay, what are we building?”

You start with one or two engineers, talk to a LOT of customers, and iterate quickly on feedback to make your first twenty customers fall in love with your product.

You gradually scale up as you hit product-market fit.

It’s the same with a sales team.

Go out and hire a couple “full-stack” sales reps, listen to their calls, and iterate until you figure out who your ideal customer is, and what messaging is resonating in-market.

Once your AEs begin filling up their calendar because of their prospecting activities, it’s time to hire a BDR to repeat the model. Trying to figure out both roles simultaneously is a huge distraction.

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4. Sometimes you have to slow down to speed up.

This is true in every department, but it’s especially true in sales: faster is not always better

We always want every dollar invested in sales to directly translate to revenue. But you can’t put rocket fuel in a motorcycle.

It’s easy to look at hiring someone in sales operation or sales enablement as overkill for a small team.

“But a sales ops manager won’t be carrying a quota! That’s just a cost center, not a profit center,” one might say.

Here’s the thing: if you can make every rep 20 to 50% more effective because of sales enablement, isn’t it going to have a bigger net effect than putting that budget towards another rep?

And if reps spend less of their time wrestling with the CRM, inputting data, building out lists, and the sales leader spends less time struggling with generating reports from Salesforce, because you hired a sales ops manager to take care of this, the effect will be multiplied across the entire sales organization.

Here’s another example:

We closed a good sized deal with a new customer last month and celebrated.

What's even better? They came in as a lead and went from a stage 0 to Closed:Won without any other stages in between.

Three weeks later I hear from Customer Success that they're cancelling and asking for a refund. Turns out that our software doesn’t meet the needs of their biggest use case.

We didn't learn that until we got into implementation.

So what happened? They rushed the sales process. And we let them.

Closing deals is great. Shortening cycles is great. But if churn and clawbacks happen as a result of not moving them through the buying process in a controlled way, we could be doing more damage than it's worth.

Make sure there's true alignment before taking them on and don't let prospects bypass your sales process.

5. Marketing and sales need to operate as one team.

Ah, the classic struggle between sales and marketing.

“The leads are weak!” — Sales

“The leads are weak? YOU’RE weak!” — Marketing

We realized a few months ago that something troubling happened: silos had clearly formed.

Marketing and sales were physically on different floors. They had separate Slack channels. They rarely interacted. And it showed.

Sales reps ignored marketing content. Marketing pumped out blog posts, social media graphics, and lead magnets every month, but sales didn’t trust that they would result in good leads, so they never shared them.

Marketing had a general idea of who our perfect customer is but didn’t fully understand what keeps them up at night, how they talk about their problems, or why they might need Proposify.

Reps took to LinkedIn and started creating their own content, but didn’t get input from marketers whose profession is creating content and clearly could help them.

Marketing was scored on trial signups, MQLs, and activation metrics, but when we dug into the numbers, only a small percentage were turning into sales accepted leads, and even fewer qualified opportunities.

Something needed to change.

After much discussion here’s what we did:

  • Marketing and sales moved onto the same floor and sat with each other. Not a silver bullet by any means, but it meant they were now interacting with, and building empathy for one another.
  • Marketers started listening to sales reps calls and hearing the voice of the customer, learning what their challenges are, and why they are looking for a solution.
  • Marketing started focusing on KPIs further down the funnel: SALs and new pipeline added. It’s natural for marketers to get excited by big numbers. Thousands of leads generated from a content piece or a trade show feels great. But if those leads don’t translate to revenue, because they’re the wrong leads, it doesn’t matter.
  • Sales and marketing started sharing each other’s content. Sales began contributing ideas to the blog. Marketing produced the State of Proposals statistical report and sales was excited about using it in cold outreach and at conferences.

And “magically” things changed:

  • Our inbound SDR, Laura, hit her meetings booked target for October
  • AEs began booking good calls from cold-prospecting content leads
  • October had the most pipeline generated from inbound in a month

There’s still room to improve, but in a very short time the two departments are much more closely aligned than they’ve ever been.

6. Cold-calling isn’t dead.

If you visit Hubspot’s Inbound event you’ll often hear the term “interruptive” marketing thrown around. Outbound is dead! Cold outreach is dead! Nobody answers their phones!

The funny thing is that if you’ve ever downloaded a lead magnet from Hubspot, they have an army of sales reps calling you.

Because there’s been such a shift to inbound over the years, there’s a lot more brands creating content, competition for eyeballs has gotten a lot tougher, and many sales teams have abandoned the phone, which presents a huge opportunity—suddenly people are answering their phone again.

Our very small team of three AEs started prospecting heavily and in two months booked meetings with 18 new leads purely from cold calling—many of which turned into piped opportunities.

Even better, we’ve found that cold calling people who download lead magnets (“content leads”) has helped us gradually build up our pipeline. This is combined with calling leads that are further down the purchasing funnel, like people who make demo requests or start free trials.

A sales team shouldn’t rely purely on inbound leads from marketing. They have to learn how to build pipeline through prospecting. When done right, cold calling can be a very effective medium.

7. Understand and treat every buyer as unique.

Many companies have an ICP, an ideal-customer-profile, they sell to. But too often they only look at the account level.

A company might say, Our ICP is healthcare providers, gym franchises, or sales trainers. Some go even more broad and just say “small businesses”.

But an ICP goes deeper than just company size and industry. Those are surface level firmographics. What other attributes does your ICP company have?

When we dug into our ICP we realized that our best customers share certain attributes:

  • They’re in competitive markets.
  • They have an established sales process.
  • They’re aggressively scaling.
  • They send a high volume of proposals with minor variations.
  • They care about branding and design, and have in-house marketing support.

Furthermore, who actually buys at these companies? A lot of companies have a one-size-fits-all approach when they’re pitching to prospects.

When we looked at all the different job roles of our prospects and their jobs-to-be-done, we realized that they are buying our product for very different reasons.

  • Marketing wants the documents sales reps send out to reflect the brand and be well-designed. They need consistency and control over what gets sent out, but they don’t want to be the bottleneck in the process.
  • Sales leaders want to hit their targets. To do that, they need their sales reps to spend less time copying and pasting from past content, or wrestling with Word formatting so they can get proposals in front of the buyer faster. The faster that happens, the less chance of a competitor coming in and stealing the deal.
  • Sales ops wants data from sales documents to be accurately reflected in Salesforce (and vice versa) and for reps to be more efficient.

We had to understand those different wants and needs, and use them in our positioning and messaging.


If you couldn’t tell from these lessons, the only consistent thing about being a co-founder and CEO is change. I continue to learn and grow as a salesperson and leader as we work hard to scale Proposify too.

What aspect of sales has taken you by surprise lately? Click over to my LinkedIn to join the ongoing discussion about these sales lessons and more.

7 Surprising Sales Lessons I Recently Learned About Scaling to $10M ARR

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