What Breaks When Companies go From Series A to B?

In a previous article, I talked about what often breaks in companies and sales organizations when scaling from Seed to Series A.

The themes are very similar in this next stage when it comes to having the right people and processes, but what I’m going to dig into here are the specific fail points of companies moving from Series A to B that often aren’t realized or addressed until years later.

You can circumvent these common mistakes by watching the three things that often break in companies scaling from Series A to B in the video below.

  1. Support roles for the sales org: sales operations and enablement;
  2. Hire the experience you need today; and
  3. Invest in an inbound engine.


Support roles for the sales org: sales operations and enablement

As companies grow and scale, they often underestimate support roles for the sales organization and under-budget for them.

On the other hand, marketing teams are supported by PR agencies, web developers, design and brand firms, performance marketing agencies, etc. In sales, we tell our managers and reps to figure it out. 

If you want to be successful and grow fast, your sales team needs sales operations and enablement support. A good estimate threshold is when you get to 6 to 10 people on your sales team, and you need to supercharge their performance and give leaders the bandwidth to lead.


Hire the experience you need today

When it comes to hiring your first VP of sales, which is usually happening around now, hire for the stage you’re at today. For example, if you’re at $7 million and your goal is to get to $20 million over the next year and a half, hire someone who has been there and done it once or twice.

Don’t hire the big CRO, and don’t try to make someone who’s barely been a manager your VP either. You need an experienced person who’s seen around the corners. And again, the corners that are specific to your challenges for scaling from $7 million to $20 million.

This is also the time when you have to start thinking about specialists and possibly make some hard decisions. 

Seed to Series A and “startup” people do a little bit of everything, and they love it. As you scale, you’ll need specialists who only do two or three things at scale, which sometimes means your OGs have to move on.


Invest in an inbound engine

Do this early. Invest in an inbound engine. 

This engine could look like your sales organization leveraging LinkedIn or adding a demand-generation person to your marketing team.

Inbound is the fail point that many organizations realize too late in the game and historically have tried to scale with more and more outbound.

If you start investing in producing content on LinkedIn and producing content that builds awareness and brand over time, when you fast-forward three years down the road, it makes getting to $50 million or $100 million exponentially easier.

That’s it, my friends. My three most essential tips for executive and revenue leaders who want to successfully scale from Series A to Series B.

Jake Dunlap Skaled headshot

Jake Dunlap designs repeatable, sustainable sales models and processes that outperform industry standards. As the founder and CEO of Skaled, Dunlap helps executives around the world accelerate business growth with data-backed sales solutions. Before building Skaled, he held the roles of VP of Sales at Nowait (acquired by Yelp), Head of Sales + Customer Success at Chartbeat, and VP of Sales at Glassdoor (acquired by Recruit Holdings for $1.2 billion in 2018).

You can find him on LinkedIn.

  • Originally published December 22, 2020, updated January 7, 2021