Todd, the founder of a Series A SaaS startup approaching $10M ARR, offered an extra $40k base, 1% in equity, and a signing bonus to secure Janine as his next Chief Marketing Officer.
Janine was his dream candidate. She’d led marketing teams at blue chip companies, overseen international expansion, and launched new product lines that went on to become household names.
He was sure she was the perfect person to help him take his company from $10 to $100M ARR.
So, he was surprised when he got early feedback from the team that things didn’t seem to be working out.
Janine built an incredible 3-year strategic plan, was thoughtful about market positioning, and made big revenue commitments — if she could get the paid ad spend, PR firm, internal headcount, and investment in product localization she needed to deliver on her plan.
But, she didn’t really do all that much of what other people considered “the work that needed to be done.”
She didn’t spend time deeply learning the product, listening to individual customer calls, writing copy for new feature launches, or suggesting targeted SEO changes.
A few months in, churn took a bad turn.
Product-market fit wasn’t as solid as Todd thought.
And when he had to get ruthless about costs to give the company the runway to make sure they built a product that turned buyers and users into raving fans, Janine’s big comp package didn’t make the cut.
So, what went wrong?
Todd hired someone who specialized in making $100M+ companies successful because that’s where he wanted his company to be in the future.
But, it’s not where the company was — and Janine’s skillset wasn’t what the marketing function needed — right then.
There tend to be three distinct growth stages (with sub-stages) on the path from $0 to $100M+.
- Product-market fit: You might hear this called the zero to one stage. It's often described as $0 to $3M — like in JooBee Yeow's graphic above — or $0 to $10M. In this stage, you're trying to build a product that attracts raving buyers and users (aka strong market demand and referenceability) by understanding your target customer's needs and solving their pain points in a way that they're willing to pay for. There is a lot of testing and iterating.
- Go-to-market (GTM) fit: This stage is about achieving a repeatable, scalable, and profitable model for reaching, acquiring, and retaining customers. It can be a product-led or sales-led motion, but needs to be something that you can predict and replicate with at least one consistent customer segment.
- Multi-market fit: At this stage, you reproduce your success in finding product-market and GTM fit in adjacent markets with the same or related offerings in order to reach a greater scale. This often looks like building new products or monetizable features, broadening your ideal customer profile (ICP), or exploring international markets.
Some startup executives have seen all three stages multiple times. But, those people are rare. By hiring them, you’re likely overpaying for experience that’s not immediately relevant to your org in the hopes that the exec will stay with you for 5-10 years.
Given that the average tenure for CMOs at venture backed tech startups is 17 months, that’s a big bet to make.
Most companies — especially VC-backed ones — are better served by hiring someone who has seen the stage that they are currently in and will be in over the next 18 to 24 months.
Think about scaling a company like competing in a triathlon.
Why hire the best triathlete when you’re only going to be swimming for the next 2.5 years?
Go out and hire the fastest swimmer. Bonus points if they know how to coach others to swim too.
The Four-T Playbook
Every edition, I share a proven tip, trick, tactic, or template. This time, it's a:
👉 Tip: Take time to learn the characteristics of each stage of growth — for the company overall and for each function within it.
In lieu of spending 20 years working at various sizes and stages of companies, learn from others who have.
Read Molly Graham’s Lessons and consider signing up for JooBee Yeow’s Step Up MBA course. The exclusive BUSINESSOFPEOPLE discount code for 50% off expires on January 16, 2026.
Final thoughts
Have you ever hired a Janine? Hit reply and tell me about it.
Or, let me know what people topics you'd like to see me cover this year.
Until next time,
Melissa