Choose the cohort
Agree the segment, seller group, baseline, shared brief and quality bar. Observe how your managers and sellers work before deciding what to change.
A PERSONAL POINT OF VIEW FOR ZACH REGO · TRIPLE WHALE
Zach, this page
is the sales motion.
You’re looking for a sales leader who already uses AI to improve execution. I wanted to show you how I work.
From finding the right prospect to researching the account, building a personal point of view and carrying that context into every follow-up.
Jason Wickman · Founder, Agilidy · Prepared October 5, 2026
Commercial judgment+AI-assisted execution+Accountable follow-through
WHY TRIPLE WHALE CAUGHT MY ATTENTION
You sell data that leads to action.
I see the same opportunity in sales.
Your VP Sales posting connects AI fluency with repeatable sales motions, manager coaching, pipeline generation and expansion. That combination is what made me stop and research the business.
My hypothesis: use AI to make thoughtful preparation and personal follow-through repeatable across sellers. Keep the commercial judgment with the people who own the number.
5 sales leadersDirect reports in the VP Sales mandate
30+ sales teamOrganization described in the posting
Practical AI fluencyA stated requirement, demonstrated here
EXPLORE MY SALES EXECUTION WORKFLOW
One thesis, carried all the way through.
Select a step to see the work, the output and what travels to the next interaction.
STEP 01 / 07
Find the right accounts
Start with fit and a reason to care.
AI helps surface relevant companies, buying signals and the right revenue leaders. I decide where I have a useful point of view before investing in outreach.
Account selection · this example
ACCOUNT: Triple Whale
PERSON: Zach Rego, Chief Revenue Officer
SIGNAL: Live VP Sales opening focused on AI fluency, repeatable sales motions and expansion
MY HYPOTHESIS: Show the work behind an AI-assisted revenue engine.
An account and a reason to engage.
This microsite is the working artifact. Email, call and CRM outputs above are examples of the proposed connected workflow.
EXPERIENCE THE CONTEXT
The assistant knows
why this page exists.
Ask about the Triple Whale thesis, question the pilot, or request a rehearsal of the follow-up conversation. The assistant is grounded in this account brief and Jason’s proposed approach.
“What would you test first?”“How would this help our managers?”“Rehearse the follow-up call.”
On-demand AI demonstration. Voice and text input are supported. It can explain and rehearse; it does not send outreach or book meetings.
WHERE I WOULD APPLY THIS AT TRIPLE WHALE
Different motions.
The same discipline.
Make the first conversation about the brand’s business.
Choose a focused seller cohort. Build account briefs around acquisition economics, measurement needs and operational priorities. Use those briefs to create relevant POVs and prepare discovery.
Measure the movementQualified conversations and pipeline per rep, preparation time, stage conversion.
MAKE THE CAPACITY QUESTION CONCRETE
What could better preparation give back?
Change the assumptions to explore preparation capacity. Then test whether that time produces better conversations.
24hours / week
Potential preparation capacity returned across this cohort.
Illustrative arithmetic, not a measured result or revenue forecast. Saved time only matters if conversation quality and pipeline improve.IF I OWNED THE FIRST 90 DAYS
Prove a useful motion.
Then make it repeatable.
Run the pilot
Build account-specific POVs and a connected follow-up playbook. Compare a similar cohort. Inspect relevance, preparation effort, qualified conversations and next-step quality.
Make the scaling decision
Review pipeline movement and cost. Coach the managers, document the playbook and scale the effective parts. Recruit and hand off to long-term ownership where appropriate.
Scorecard
Qualified pipeline per seller · Conversation conversion · Preparation effort · Follow-through quality · Workflow cost
WHY I BUILT THIS FOR YOU
I lead the work.
I also build it.
I’m Jason Wickman, founder of Agilidy. I bring 25+ years across marketing, sales and technology, including Microsoft field and partner sales, CRM practice leadership and Challenger coaching.
I sold my CRM practice to Avtex and helped launch the US business for Process Analytics Factory, later acquired by Celonis. Today I work with a handful of clients and build AI-supported sales workflows myself.
My fractional model is to get in, own an agreed outcome, deliver results, help recruit the long-term owner and hand off for lasting success. This page is a small example of how I would approach the work with your team.
See another account-specific POVA PERSONAL INVITATION
Zach, I’d welcome
your perspective.
If this looks like something worth exploring, I’d enjoy comparing notes on where a focused pilot could help your team.
Connect with Jason