Hey there! I’m Calvin Wiltermood, Advisor, Trailway Growth
Trailway Growth was started to help early founders and lean teams successfully out compete their larger incumbents.
We want to even the playing field - and so we love email. The audience targeting is pin-point. It’s fast. It’s affordable. In the era of Tik Toc attention spans, you need a way to increase ROAS - yet it’s in near freefall across all channels. Unlike other agencies or consultants, we pair DFY services with deep involvement.
We’ve helped clients fix their pricing, their sales process, their targeting, build lead magnets - even helping them completely refresh their product market fit strategy with new value propositions.
There is no other agency that is as deeply involved with their clients as Trailway Growth. You won’t see a fancy poweroint telling you obvious platitudes like “pick low hanging fruit.” Instead, you’ll have new partners to help you exceed your goals.
Prior to Trailway Growth, I worked through college as a manual laborer doing landscaping & house painting.
Once graduated, I saved $1,000 and moved to NYC. After sending 1,027 applications (And spending my last $20 on MTA passes), finally got my break working as an SDR for a UK-based AI startup - sourcing deals with household names including Bain & Co. While always favoring the phones, email’s scalability was fascinating.
I wanted to crack the code. I moved on to a Japan-based customer data company, writing the playbook for the SDR org and was promoted to an Enterprise Account Executive.
That next year, we suffered a RIF, so I made the rational decision to throw what little I had into a backpack and tour 17 countries over a year in a half while starting my own company: LeadSpring.
As the founder of LeadSpring.Ai - we helped clients land their first halo brand and crack their first $100k ARR. It was an incredible privilege to help founders bet on themselves.
After closing +$600k ARR over 50 clients, the Trailway Growth team approached us for an acquisition.
LeadSpring was acquired at the end of 2024, and I’ve been amazed to watch Trailway Growth continue to elevate client outcomes. We’ve continued our partnership to ensure Trailway Growth remains at the avant-garde of go-to-market.
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