Hi, I'm Jon Caldwell.
I help B2B founders and experts
(with at least a few customers)

grow their revenue.

4x founder and military veteran with $23M+ in sales of software, services, hardware, and companies. Strategic consulting and hands-on services in positioning, messaging, pricing, and channel-agnostic marketing and sales.

Case Study: $375k MRR Added

Turned around a 3-year decline in revenues of 12% into an unprecedented 3-year 80% growth phase, setting new revenue records each year. The company grew by over 20 employees and generated an estimated $6M in new equity value. Launched paid ads, organic content and outbound systems that blew traffic blew up over 1230%, creating millions in new pipeline and contracts, plus 3400+ members signed up to a private community.

Case Study: $1.2M Added

Built outbound system and grew revenues by $1.2M in 18 months, created $5M+ of equity value. Signed enterprise deals with major clients: National Bank ($120B bank), QC Bar Association (29k lawyers), SSQ ($25B Insurance co), MTY ($400M franchise group). Went on to be acquired by Experlogix, a 200+ person software company.

Case Study: 10x EBITDA Exit

Successfully pitched on Dragons’ Den and got offers from all investors. Raised capital, grew 8x faster than the industry, hit a 76 Net Promoter Score, and sold the business to a competitor for 10x EBITDA. The sale generated a 36% annualized return for my investors.


denis brochu

Founder & Board Director, INGENO

Jon is a bright, organized, and passionate individual with a great entrepreneurial mind. Jon faced the challenge of reshaping our business development practices [...] He tackled it head-on and introduced innovative ideas, approaches, tools, and processes crucial to our growth and success. [...] Jon is a person you can trust and count on.

david squibb

President, Covenir (Constellation Software)

Former CRO, Xpertdoc

Jon is the real deal! From my first conversation with him - I knew he was unique in his abilities and raw talent. [...] What he delivered far exceeded all of my expectations! [...] I would wholeheartedly endorse him.


Founder, EdTech SaaS

The work that we've done with Jon has been nothing short of remarkable. [...] from the strategic to the tactical, all the advice and coaching that Jon has been able to give us, these last few months have created [...] much better sense of direction, and clarity and purpose. [...] if you're thinking about working with Jon, all I can say is it's absolutely worth the time. It's a 10 out of 10 for me.


Vice President, INGENO

Jon is a self-made entrepreneur with unbridled energy, creative acumen, and a deep understanding of sales strategies, market development and customer engagement. Jon was instrumental in driving unparalleled growth for our company [...] helped us implement innovative strategies to optimize the sales pipeline.


Founder, Event Management SaaS

He gave key insights that helped define our product, branding, and launch strategies. [...] Jon's expertise and insights were invaluable, and I highly recommend him to any company looking to vet and plan for product launch or growth.


Founder, Photography SaaS

[...] the app launched as a freemium service based on that discussion. [...] Downloads are also already up and we have yet to lose a subscriber [...] I just wanted to give you an update and express our appreciation for your wise counsel. We are re-energized and excited again for what the future holds.


Founder, Equipment Rental SaaS

His insights challenged our goals and gave us an objective view of our mission. Some of the news he shared was difficult to hear; but that's exactly what we needed to learn. Jon is an invaluable asset for any company launching or growing their product.


Founder, B2B RE Service

His B2B experience shaved off a massive learning curve and time for me [...] He saw my struggles as the CEO right away, [...] being a founder himself, he said, “Chris, this is actually what you're facing, and these are the strategies we need to put forth to tackle them.” [...] You quickly realize how little you know, and working with Jon was a quick eye-opener on the level of depth he understood [...] from the ads to the messaging, it's all just bundled in, and it's been a game changer. [...] I highly recommend him, and I'm looking forward to keep working with Jon.

About Jon Caldwell

I'm a military veteran, founder, father, and growth consultant. I help early- and growth-stage B2B tech companies grow. Over the last decade, I’ve raised money, started and sold a company, built and led teams, and led revenue growth for companies. I've generated over $23M in revenue for clients and myself.