I led sales at Heap from $400K to $10M ARR in ~3 years. 9 out of 10 startups that hit $1M never make it to $10M. Here are my 5 biggest mistakes and how I’m increasing the odds of doing it again at Champify—faster:
1. I was always focused on the next chunky deal
Instead, focus on building a pipeline MACHINE. Sam Blond phrases it perfectly, “Usually a company misdiagnoses a sales problem for a demand gen issue.” Religiously track how many new meetings and opps you are creating and constantly find ways to grow this number.
This will have a bigger impact than a small increase in win rate.
2. I spent a lot of time searching for unicorn reps with the exact “right” profile
Instead, invest time building the systems and frameworks to make any above average rep successful. That way, your success rate will be higher and when you do hire the truly great reps, they can be an order of magnitude more productive than their peers.
3. I over-indexed on the importance of product knowledge
I come from a sales engineer background. The reality is that while product knowledge does matter, understanding of the PROBLEMS your persona and target account face is 10x more important than knowing the product inside and out.
During training and enablement, think about ways to enable reps on the problems vs the nuance of your product offering.
4. I spent far too much time with reps in a 1-1 capacity and ended up wasting 100s of hours teaching and training on the same topics (without others benefitting)
Implement mandatory enablement every 2-3 weeks. Before you have an enablement team, IT IS THE JOB of the sales leaders to own this. Lean on experienced reps and other roles within your org to deliver these training sessions.
It’s critical to constantly level up your sales team AND do so in group settings to create space to share learnings, challenge each other, naturally compete, and scale.
5. I did my best to hire smart SDRs and get out of their way
Outbound is significantly harder today. Remove as much of the decisions that an SDR needs to make. Determine the accounts and personas they should target, enable them on the problems each person in your buying committee faces, and search for areas you can improve by using data and constantly getting feedback.
The outbound world is too hard today for junior reps to figure it out on their own.
Takeaway:
Scaling from $1M to $10M ARR isn’t about chasing the next deal or finding unicorn hires—it’s about building scalable systems, understanding your buyer’s problems, and constantly enabling your team to succeed at every level.
Don’t make these dumb mistakes I did :)