Sales execution & first-of-a-kind delivery · Calgary
Where the playbook
runs out.
The programs that matter most are the ones nobody has run before. No benchmark to price against, no reference to sell from, no template to deliver on. That is the work I want.
Currently taking on three new engagements for Q4.
The architect
Twenty-two years inside the room where the deal gets built.
Enterprise GTM executive with 22 years building commercial engines for the Fortune 500. Today I lead Strategic Initiatives for the Americas and the Global Customer Success President at SAP. Before that, eight years as a Managing Director at Accenture and seven as an Associate Partner at IBM.
I have carried a number, owned a P&L, sat on the vendor side of procurement and on the advisory side of a board. That range is the whole point — most execution problems live in the seams between those rooms.
- Mega-deal pipeline architecture
- GTM system engineering
- Complex procurement negotiation
- Executive peer-to-peer advisory
- Cross-functional team leadership
- High-growth startup mentorship
- Enterprise SaaS & cloud strategy
- Applied AI in the commercial motion
Career arc
Where the pattern recognition comes from.
Executive Coaching & Advisory
- Private coaching for commercial leaders, CIOs and Series B+ founders
- Strategic advisor, MacKay CEO Forums
Office of the CRO & President — Strategic Initiatives & Cloud
- Leading global cloud strategy for the RISE Strategic Customer Program
- Translating legacy core architectures into scalable, high-ARR cloud assets
- Orchestrating high-stakes cloud migrations for complex organizations
Managing Director
- Full P&L accountability across Fortune 500 relationships
- Led the Canada Resources Client Services Group and North American GTM sales
- Aligned complex systems integration and digital transformation programs
Associate Partner — Business Analytics & Optimization
- Built foundational data structures and advanced analytics architectures
- Led regional sales for the Chemicals & Petroleum sector
Peer-to-peer execution
Three programs. One diagnosis.
If your GTM strategy looks flawless on paper and pipeline velocity is stalling, you have an execution problem. That is the thing I fix.
The Mega-Deal Playbook
A private, outcome-driven program for commercial leaders. Master complex discovery, multi-thread executive relationships early, and move from feature-selling to strategic solutioning — expanding contract values and compressing enterprise sales cycles.
CIO Advisory Program
Private, peer-to-peer advisory for IT leaders — bridging the gap between the underlying technical architecture and the business outcome the board expects. Manage technical debt, build alignment upward, and land the migration.
Venture Scale Lab
For Series B+ founders moving away from erratic founder-led sales toward a predictable, enterprise-grade GTM engine — and accelerating the decision velocity of an executive team that has to keep pace with the growth.
Negotiation strategy & execution
Live procurement war-gaming for a specific deal in flight. Half a day, your team, your paper, my side of the table.
Work with me
Three ways in, depending on how fast you need to move.
Every engagement starts with a call and a written scope. No open-ended retainers, no discovery phase that bills for four months before anything changes.
Diagnostic Sprint
Fixed feeA teardown of the commercial motion you already run. I read the pipeline, sit in on live deal reviews, and come back with what is actually blocking velocity.
- Pipeline, forecast and deal-desk review
- Two live deal teardowns with the owning reps
- Written findings and a 90-day execution plan
Executive Coaching
Most commonOne leader, one standing slot, and access between sessions when a deal turns. This is where the Mega-Deal Playbook, CIO Advisory and Venture Scale Lab are delivered.
- Two private 90-minute sessions a month
- Direct access for live deal and board moments
- Quarterly reset against agreed outcomes
Team Programs
Per programThe playbook delivered to a full sales org or leadership team, worked against your live pipeline rather than a case study nobody in the room cares about.
- Procurement negotiation war-gaming
- Multi-threading and executive access clinics
- Manager enablement so it survives after I leave
Fees are scoped to the engagement and quoted in the proposal. Ask on the call — I will give you a number before you leave it.
A 30-minute call
You describe where the motion is stalling. I tell you whether I am the right person, and say so if I am not.
A scoped proposal in three days
Outcomes, cadence, duration and fee in writing. One page, not a deck.
Working inside two weeks
First session or sprint kick-off lands within a fortnight of signature.
The engineering of revenue
Deal velocity is a system with four dials.
Most teams pull hard on the one dial that moves least. Drag the sliders and watch which variable actually governs the number.
Projects
Still building.
Twenty-two years in and the interesting problems are still the ones nobody has solved yet. Benchside is the current one.
Benchside
A family-first hockey management platform. One schedule, one ledger, one household — even when that household spans two homes and three clubs.
Minor hockey runs on a stack of tools that were each built for the club, never for the family. Benchside inverts that: the household is the primary object, and teams, providers, associations and grandparents all attach to it.
Professional endorsement
What clients and colleagues say.
Shared with permission, attributed anonymously to protect confidential engagements.
Six months in the Mega-Deal Playbook and our average contract value is up 40%. More importantly, my team stopped negotiating against themselves in the room.
Byron is the rare advisor who can sit with the board and the engineering team in the same week and be equally credible in both rooms. The CIO Advisory sessions saved us from at least one migration disaster.
We were still selling like a five-person startup at 200 employees. Byron rebuilt our GTM engine from the ground up — pipeline reviews, forecasting, the whole system. Revenue predictability changed overnight.
Worked with me? Add a recommendation
The Mega-Deal Notes
One note a month on how enterprise deals actually close.
Procurement tactics, multi-threading patterns, forecast hygiene and the occasional teardown of a deal that went sideways. No newsletter filler, no course launch.
Get in touch
Ready to move the number?
Whether you are recruiting for a senior executive role, exploring coaching, or want to talk about an active project — go direct.
Calgary, Alberta · Working across North America and EMEA