Three things I have done, not advised on
I chose the CRM. Adoption was the hard part.
The problem. The Hercules Group had grown by acquisition into five brands. Each had its own sales team, calling on nearly the same customers, out of the same inventory, at the same prices. Two of my reps would sometimes visit one customer on the same day. Customers worked out fast that they could play us against each other.
What I did. I fixed the business before I touched the software. If 80% of a customer’s spend sat under one brand, that brand owned the whole relationship, except where a genuine specialist was needed. Then I rebuilt the commission structure so it stopped rewarding the old behaviour, and gave every customer a single point of contact. Only then did I evaluate the platforms, choose one, design the system and the screens my reps would use every day, write the training manual myself, and roll it out across the country. I restructured and redeployed the Quebec sales team in the same period.
What happened. Between 2015 and 2017 both industries we sold into collapsed at the same time. Offshore Newfoundland production fell by 16 million barrels, provincial royalties dropped by a billion dollars in one year, exploration stopped and the supply chain shed thousands of jobs. Meanwhile the northern shrimp quota was cut 78% in two years and snow crab was cut 22%. We grew more than 10%.
I built the sales organisations, not just the strategy
The problem. TELUS had an independent dealer channel that only knew how to sell retail. The mandate was to make it sell B2B.
What I did. Six dealers, and I effectively acted as VP of Sales for each of them. I wrote the plan for what a B2B rep should do all day, sat in on hiring their reps and their sales managers, built the process, and put a CRM into each dealership so they could run it. Not a deck handed over at the end. I was in it.
What happened. The channel ran at 3.3 times the performance of traditional direct sales channels covering the same territory. 85% year over year growth, the number one performing region in Canada, and I co-led the largest mobile contract TELUS had won in Atlantic Canada.
I have been the vendor on the other side of the table
The problem. At Dayforce I was accountable for the Canadian partner network, selling human capital management software through consulting partners.
What I did. Built the partner go-to-market from the inside: the ideal customer profile, the outreach, the materials, how partners engaged us. Launched a reseller programme that added 300 new logos to the pipeline in its pilot alone, and scaled the consulting relationships into two seven-figure national opportunities across North America, Australia and Europe.
What happened. 33% of national revenue came through that channel. It also means I know exactly how the people advising you get paid, because I used to be the one paying them.
And one I got wrong, recently, with my own money
At PhoneStack I bought a dialler because it was built into the email platform we already used. On paper the integration was the whole point: one system, email and calls in a single sequence. In practice it broke constantly, and support was slow enough that I could not get it working. I killed it and we built our own instead. It is not the best product on the market. It works, and I may well replace it again.
Two things that cost me money and are now the first things I look for. Integration that looks clean in a demo is not integration that works on a Tuesday afternoon. And support quality is invisible while you are buying and decisive the moment you have bought. No vendor will ever raise either one with you.
The Hercules rollout taught me the other half. My reps pushed back hard, because a new system feels like being watched and because what they were doing already worked, for them. I gave each location one day of training. It needed two or three, and a second visit. It was rough for months and took about six to land properly. The software was never the risk. Adoption was, and it always is. So when I tell you a rollout stalls at adoption rather than at the technology, that is not a theory I read somewhere.
I spend my week watching enterprise AI projects either ship, or burn a year and quietly die in pilot. Most die. That is a useful thing to have watched many times before you start yours.
Having sat on the selling side of the table means I know how roadmaps get sold, and I know how “AI-ready” gets defined by the people selling AI. I also know the part nobody selling it will tell you: which of these projects reaches production, and which ones consume a year and get quietly shelved.
There is a pattern in all of it. Hercules had five brands whose systems and teams had stopped lining up. Dayforce customers were running several payroll systems that never agreed with each other. At PhoneStack I now choose tools on whether they connect, not on their feature lists. The problem I keep being handed is a business whose systems have sprawled and stopped talking to each other, which is what tends to happen to an owner-led firm somewhere between 10 and 100 people.
All of which means I have interests to declare, so I declare them, in writing, on this page, before you have to ask. Navigator is the one room where the only interest I’m paid to serve is yours.
My current roles, declared
- Amazon Web Services (contract) Partner Marketing Director, global System Integrators, GenAI and cloud go-to-market, North America.
- Blue Harbour Solutions Founder. Navigator Assessment™, Navigator Advisory™, BlueAnchor and WildEcho.
- PhoneStack Co-founder and CEO. An AI phone service, a separate company, not a Blue Harbour product.
Before
- Dayforce (Ceridian) 2019-2022Director, Channel Sales, Canada
- The Hercules Group 2013-2018Regional Sales & Marketing Manager, 17 branches
- TELUS 2009-2013Senior Manager, Independent Channel
- Xerox 2005-2006Sales, Dallas Fort Worth territory
Recognition
- President’s CircleDayforce (Ceridian), 2020, at 130% of target
- Pinnacle AwardTELUS, 2011, on 85% growth
- President’s ClubXerox Canada, 2006, at 135% of target
- Top-ranked portfolioNorth American partner marketing, AWS, 2024
Four companies, four times, across twenty years. One is luck.
Qualifications
- Dalhousie UniversityBCom, Marketing Management
- Lean Six Sigma Green Beltvia Xerox Canada
- Certified Predictive Index® AnalystCovey: Great Leaders, Great Teams, Great Results™