Fractional Sales Leadership · B2B Growth

Your revenue is stuck.
We build the system
that unsticks it.

One Wolf Advisors delivers senior sales leadership without the full-time executive overhead. We specialize in the $20M–$100M inflection point, where founder-led growth must become process-driven scale.

Book a Strategy Session See the Results

$700K → $50M+ Revenue Built

137% YoY Growth Delivered

25+ Years Sales Leadership

150%+ Quota Attainment

The Inflection Point

"Founder-led sales is a superpower at $1M ARR. It becomes a bottleneck at $10M — and a liability at $20M."

Revenue closes because the founder is on the call — not because the team is equipped
Pipeline is a gut feeling, not a data-driven forecast
New hires take 6+ months to ramp — if they ramp at all
Win/loss reasons are unknown; the playbook lives in someone's head
Sales and marketing aren't aligned — and the leads show it
Retention is bleeding because sales sold to the wrong buyer

What We Do

Fractional sales leadership that actually leads

We embed as your senior sales executive — driving strategy, building process, and coaching your team — at a fraction of the cost of a full-time VP hire. Every engagement is built around measurable outcomes, not hours billed.

GTM Strategy & Rebuild

We audit your go-to-market motion from top of funnel to close, identify where revenue is leaking, and design the system that fixes it — territory structure, ICP refinement, and qualification standards included.

SDR Function Build-Out

Free your AEs to close. We build your first (or next) centralized SDR function — hiring criteria, outreach cadences, sat-rate benchmarks, and tech stack integration — so top-of-funnel discovery runs without you.

Playbook & Enablement

The founder's intuition becomes a documented Value Selling framework. Every rep gets the same playbook, the same qualification standards, and the same 60-day ramp path to qualified pipeline.

Forecast & RevOps

We implement trend-based performance reporting that gives leadership full visibility into conversion, velocity, and rep productivity — tightening forecast accuracy from ±35% to ±10% or better.

Team Scaling & Coaching

From hiring profiles to 1:1 coaching frameworks, we build the management layer your growing org needs. Reps ramp in 60 days. Managers learn to lead, not just manage. Culture becomes a competitive advantage.

Retention & Expansion

Growth that leaks is not growth. We align sales and customer success through escalation systems and cross-sell frameworks that protect ARR and turn existing accounts into your most efficient revenue source.

Proven Track Record

Results that move the number

HomeBuddy · VP of Sales 137%

YoY new customer growth delivered during full company acquisition. Discovery rate tripled (5%→15%), win rate nearly doubled (31%→52%), retention lifted from 55% to 78%. $141M revenue target — 109% to quota.

HomeBuddy (Acquired by QuinStreet)

JT Packard & Associates · VP Sales $50M+

Built sales organization from zero — two people, no infrastructure — to a 30+ person division generating $50M+ in revenue. Earned back-to-back Inc 500 rankings (#332 and #245) over an 8-year growth arc.

JT Packard & Associates · Inc 500

Accruent · VP Sales Americas 150%+

Exceeded $30M net new ARR quota across 7 product lines. Cross-sell framework generated $8M in expansion revenue. Pipeline velocity up 25%. President's Club recipient. Promoted within 18 months.

Accruent · Fortive Corporation

About Jennifer Cason

The leader who walks into dysfunction and delivers anyway

Jennifer Cason has spent 25+ years building, breaking, and rebuilding sales organizations at the $20M–$100M inflection point — the stage where most revenue engines stall. She doesn't need a functioning machine handed to her. She finds the broken parts, fixes them fast, and builds the system that scales.

At HomeBuddy, she inherited a fragmented sales motion and rebuilt it end-to-end — tripling discovery rates, nearly doubling win rates, and delivering 137% YoY growth through a full company acquisition. At Accruent, she exceeded a $30M net new ARR quota at 150%+. Earlier in her career, she built JT Packard from $700K to $50M+ — earning back-to-back Inc 500 rankings.

The pattern across every role: walk into complexity, stabilize fast, build process, and deliver results. That's what One Wolf Advisors brings to your organization.

HomeBuddy VP of Sales · $141M Target

Accruent / Fortive VP Sales Americas · President's Club

Learning Pool VP of Sales · NA · 12-Person Org

JT Packard VP Sales · Built $700K → $50M+

"I walk into dysfunction, complexity, or a stalled growth engine — and I deliver results anyway."

520% Revenue increase built at JT Packard over 8 years

60 days Average rep ramp time to qualified pipeline

±10% Forecast accuracy achieved (from ±35% at Learning Pool)

3× Discovery sat rate improvement (5% → 15%) at HomeBuddy

How We Engage

The 90-Day Revenue Foundation

Phase 1

Days 1–30

Audit & Stabilization

Shadow active deals to document founder intuition into repeatable frameworks
Cleanse CRM pipeline — separate vanity deals from high-velocity opportunities
Audit SDR/BDR scripts and sat-rate conversion gaps
Evaluate tech stack for rep productivity visibility

Phase 2

Days 31–60

Process Implementation

Launch centralized SDR function — free AEs to focus on closing
Roll out data-driven sales playbooks and scripting
Separate acquisition and retention roles (hunter/farmer model)
Implement 60-day rep ramp program for immediate pipeline generation

Phase 3

Days 61–90

Scaling & Expansion

Execute cross-sell/upsell framework across existing accounts
Align Sales and Customer Success through retention systems
Establish weekly marketing alignment for campaign-driven pipeline
Transition to board-ready trend-based performance reporting

Self-Assessment

The Founder-to-Leader Sales Audit

If you check fewer than 5 of these boxes, your revenue isn't predictable — it's lucky. Let's change that.

You have a dedicated SDR team owning top-of-funnel discovery — not your AEs

Your discovery meeting attendance rate is consistently above 90%

AEs generate at least 35% of their own pipeline through outbound

You have a documented sales playbook every rep follows end-to-end

New hires reach qualified pipeline within 60 days of start date

You have granular visibility into conversion rates, velocity, and revenue per rep

Sales and retention roles are separated — hunters hunt, farmers grow

You have a structured expansion plan for cross-sell and upsell in existing accounts

Sales and Customer Success have a formal escalation system to protect ARR

Ready to stop guessing what next quarter looks like?

Book a complimentary 30-minute strategy session. We'll walk through the audit together and show you exactly where your revenue is leaking — and how to fix it in 90 days.

Schedule Your Audit Call

jennifer.cason91@gmail.com 608.225.0684 linkedin.com/in/jennifercasonvpofsales

Your revenue is stuck. We build the system that unsticks it.