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.
What People Say
Featured testimonials from clients who have worked with Thomas
Thomas didn’t just teach me how to sell (though I still hear upfront contract and Did they confirm that timeline for you? in my sleep). He taught me how to lead: how to inspire, coach, and actually manage a sales team. He also gave me the mindset tools to survive the rollercoaster of this job and come out stronger.
A lot of people talk about mindset, Thomas actually lives it. You see it in how he coaches, how he leads, and how he shows up.
If you bring Thomas into your orbit, expect to be pushed, challenged, and fully supported (his coaching sometimes even doubles as therapy). You’ll come out the other side better and with a lot more money.
We’ve had weekly coaching sessions for over a year since I joined as the first Head of Sales at my company. It has been a pleasure to strategize and collaborate with him. He offered valuable insights and support as I transitioned in the Head of Sales role and has continued to be a partner with me as I’ve scaled my sales team and our revenue.
His ideas have consistently led to immediate, positive results.
Beyond his coaching, I love the content he creates on TW Sales. Thomas started creating this just purely as a passion project which I think is why it truly resonates. I frequently reference his TW Sales blog with my team—it’s concise, insightful, and grounded in real sales experience. His content covers the fundamentals of effective sales practices in a way that’s practical, engaging, and highly actionable.
Working with him has been impactful, and I love the clarity and conviction he brings to every conversation.
Had great insights on being ruthlessly focused and building hypotheses-driven sales strategies which helped me structure Nodalli’s sales process from the ground up.
Even with five founders in the group, Thomas gave each of us genuine 1:1 attention, tailored follow-ups, and space to shape the flow of the program through his constant feedback loop. I left every session more prepared and confident than the last.
Featured Speaking
Hear Thomas discuss sales strategies, mindset, and leadership on podcasts and interviews. Learn from real conversations about building scalable revenue systems.
Art & Science of Complex Sales
Thomas unpacks his philosophy on how to build a winning sales team culture. Covering team-first thinking, belief over pressure, coaching as a leadership tool, and the simple metrics that actually drive results.
SaaS Stories
Thomas shares insights on scaling SaaS companies, building repeatable revenue engines, and the journey from $1.5M to acquisition.
Sell Me This Pen
Thomas dives into what it really takes to build a winning sales culture from the ground up with practical frameworks and real examples.
SalesTO: Building Winning Sales Team Culture
Thomas spoke at Sales Toronto Event to share his playbook for building strong sales team culture and how you can better support your sales team to achieve massive results.
Connect with Thomas
I work with founders, sales leaders, and startups to build scalable revenue strategies and high-performing sales teams. Whether you’re looking for advisory, coaching, or fractional CRO services, I’m here to help.