About Thomas Waites

TW Sales focuses on building and scaling revenue at tech startups. Here you’ll find practical frameworks and real-world strategies for salespeople, sales leaders, and founders driving growth.

I’m Thomas Waites and scaling revenue at startups is what I do best.

I’m the Founder of TW Sales Inc., where I provide Advisory, Coaching, and fractional Chief Revenue Officer (CRO) services to tech startups. I primarily partner with founders and sales leaders at Seed, Series A, and Series B companies to build scalable, repeatable, and sustainable revenue systems. I work with companies across the United States, Canada, and the European Union. My mission is to empower startups to unlock their full revenue potential through tailored strategies and hands-on support.

Previously, I served as the Chief Revenue Officer (CRO) at Median, a rapidly growing tech company. I first joined as an Advisor, serving in that capacity for two years. When I began advising Median, the company operated as a purely product-led, SMB-focused business with no sales team. I built the company’s first revenue organization from the ground up, hiring the initial sales team and Head of Sales, implementing structured sales processes, and transitioning the business to a primarily sales-driven revenue motion. After that foundation was in place, I stepped into the CRO role to accelerate the transformation. I led the move upmarket from SMB to Enterprise customers, transitioned the business from a one-time fee model to Annual Recurring Revenue (ARR), and built out the Account Management function to support expansion and retention. I now continue to advise the Median CEO and sales leadership team.

Before that, I was the Vice President of Sales & Strategic Accounts at Together, a global B2B SaaS company. I joined Together when they only had $1.5M in ARR. I rapidly scaled our revenue (see: my favourite LinkedIn post) and played a key role in driving the growth that led to our successful acquisition by Absorb at a premium valuation- my third successful acquisition to date. I put my heart and soul into building Together. And had an incredible amount of fun with my teams along the way (see: We Sell Together).

Outside of my core roles, mentorship is a calling for me. I am proud to be a Coach and Expert-in-Residence at two of Canada’s leading tech startup incubators, Communitech and DMZ, where I work closely with startup founders. I also volunteer as a mentor and speaker with programs like Women In Tech Sales Bootcamp and Palette Skills SalesCamp. Additionally, I founded The Sales Network, a free mentorship and peer-to-peer network for sales professionals looking to connect and grow together.

Based in Toronto, Canada, I am an alumnus of Wilfrid Laurier University (BA in Philosophy, Political Science, and Economics) and Queen’s University (MA in Economics).

Join me on this journey as we explore the world of sales and revenue growth together.