Copilot adoption
Where a customer is investing in AI for sellers, position Pitstop around measurable behavior change, coaching and execution.
PREPARED FOR EMMETT · PITSTOP
If I owned the sales outcome at Pitstop.
Emmett, I kept coming back to our conversation about Microsoft co-sell. I wanted to make the idea tangible: how I would turn Microsoft relationships into specific Pitstop customer pursuits, not simply ask the field for introductions.
Watch my personal noteSee the co-sell motionA PERSONAL NOTE FOR EMMETT
Make Microsoft co-sell mean something to the seller.
“Co-sell only becomes valuable when you give the Microsoft seller a reason to care.”
I spent twelve years at Microsoft. The field does not need another partner asking for access to customers. It needs a useful idea tied to an account outcome it already cares about.
Personalized video
The personalized narration for this POV is complete. The visual version is being assembled around the Microsoft co-sell story. This page is designed so the finished video can drop directly into this section without changing the thesis.
THE MICROSOFT CO-SELL THESIS
Attach Pitstop to outcomes Microsoft sellers are already trying to create.
Microsoft is putting Copilot and agents into seller workflows. Microsoft also built its own AI coach to support more than 64,000 commercial employees. That creates a relevant conversation for Pitstop: beyond giving sellers AI, how does an organization know whether sellers are actually getting better?
Dynamics transformation
Connect CRM process change with how consistently the sales team actually executes the desired methodology and behaviors.
Seller productivity
Give sales leadership evidence of where execution is improving, where coaching is needed and whether new ways of working stick.
HOW I WOULD RUN THE MOTION
Start with the customer signal, not the partner introduction.
Customer signalMicrosoft accountMS account teamCustomer buying committeePitstop hypothesisPersonalized POVCo-sell introductionPitstop engagementMeasured coaching outcome
For each pursuit I would research the customer, identify the commercial reason Pitstop matters, map the Microsoft account team and customer decision-makers, and build something the Microsoft seller can actually use to advance the conversation.
WHY PITSTOP FITS THE STORY
Microsoft can help sellers work differently. Pitstop can help measure whether they sell better.
Practice
Pitstop uses AI role-play so sellers can prepare for realistic customer situations before the interaction.
Coach
Real interactions and practice become specific coaching priorities rather than occasional manager feedback.
Measure
Rep, team and company views create evidence of execution and improvement against a defined sales standard.
Pitstop product descriptions reflect its current public positioning. The Microsoft co-sell motion on this page is my proposed commercial strategy, not a claim of an existing Microsoft partnership or endorsement.
WHAT I WOULD PUT IN FRONT OF MICROSOFT
Not “introduce us.” A reason to engage Pitstop in a named account.
Customer situation
A sales organization rolling out Copilot, transforming Dynamics 365, onboarding a major seller population or trying to operationalize AI across revenue.
The Microsoft seller's story
“We are helping you change how sellers work. Pitstop gives leadership a way to practice, coach and objectively measure whether the desired selling behaviors are improving.”
THE FIRST 90 DAYS
Personally build it. Prove it. Then scale it.
Days 1–30
Define the Microsoft-aligned Pitstop plays, identify target account signals, map relevant field relationships and build the first named-account POVs.
Output: prioritized pursuits and a repeatable account hypothesis.Days 31–60
Open field and customer conversations, refine messaging from evidence, create pipeline and document what earns engagement.
Output: active co-sell pursuits and a working playbook.Days 61–90
Advance opportunities, measure conversion and coaching outcomes, establish the operating cadence and determine where additional people are needed.
Output: measurable pipeline and a motion Pitstop can scale.WHY ME
I know how Microsoft sellers think because I was one.
I bring 25+ years across sales, marketing and technology leadership, including twelve years at Microsoft. My model is hands-on fractional leadership: I personally build and prove the GTM motion, use AI to compress the research and preparation, and keep humans focused on judgment, relevance and relationships.
AI does the research. I create the reason to engage. Microsoft creates leverage. Humans build the relationship.
EMMETT, THIS IS WHAT I MEANT.
Let's make the Microsoft co-sell idea concrete.
I am not looking to advise from the sidelines. I would personally help build the motion, create pipeline, establish a repeatable Microsoft co-sell play and help scale the people around it.
Connect with Jason