Fractional Sales Leadership · Chicago & Midwest

Senior sales leadership,
built into your business
not just brought in for a meeting.

We partner with startups, mid-market companies, and PE-backed businesses as embedded growth leaders — designing the teams, processes, and go-to-market strategies that create lasting revenue.

20+
Years of sales & operational leadership
25+
Person sales orgs built from scratch
30%
YoY revenue growth driven to PE exit
$30B+
In client revenue advised across industries
"Consulting gives you a framework. Fractional leadership gives you the relationships to make it actually work."
What We Do

Built for companies that need more than a playbook.

Most growing companies don't have a strategy problem. They have a people-and-process problem — a founder still closing every deal, a team without structure, a pipeline that lives in someone's head. We fix that, from the inside out.

01
Sales Organization Design & Build

We build sales organizations from the ground up — defining roles, hiring profiles, territory structures, and team architecture. Whether you need a single BDR function or a full-stack sales org spanning AEs, channel partners, and digital marketing, we design it to scale.

02
Revenue Operations & Process Design

We design the systems that make sales teams predictable — CRM architecture, pipeline management, forecasting, and KPI frameworks. Your team shouldn't be running on instinct and spreadsheets. We build the infrastructure that gives leadership visibility and reps clarity.

03
Go-to-Market Strategy

From market segmentation and ICP definition to territory design and competitive positioning — we help you stop selling to everyone and start winning with the right customers. We've redesigned GTM strategy for businesses ranging from early-stage startups to $30B global enterprises.

04
Sales Compensation & Incentive Design

Incentive plans that don't align with business goals create expensive misalignment. We design compensation structures that motivate the right behaviors, reward the right outcomes, and are simple enough for your team to understand and own.

05
Team Coaching & Leadership Development

Systems are only as strong as the people running them. We coach sales managers and individual contributors to raise the floor of your team's performance — through structured 1:1s, deal coaching, pipeline reviews, and skills development built around your specific market.

06
PE-Backed Growth & Exit Readiness

Private equity-backed companies face unique pressure to professionalize revenue operations fast. We've helped PE-backed businesses build investor-grade sales infrastructure, drive year-over-year growth, and position the commercial function for successful exits.

Our Approach

We don't hand you a deck and disappear.

We believe the most important work happens at the intersection of strategy and people. The best sales infrastructure in the world fails if the people behind it don't trust it, understand it, or own it.

That's the difference between consulting and fractional leadership — and it's why we do what we do.

"Consulting gives you a flash of the people. Fractional leadership lets you understand the people behind the systems — and really influence lasting change."
01
Embed, don't advise

We work inside your business — attending your meetings, learning your customers, understanding your team dynamics. Real change requires real presence, not a monthly report.

02
Diagnose before prescribing

We don't arrive with a predetermined playbook. We spend time identifying the specific gaps — structural, behavioral, or strategic — that are actually limiting your growth before recommending a path forward.

03
Build for ownership

Everything we design is meant to be owned and operated by your team long after we're gone. We don't create dependency — we build capability.

04
Operate from first principles

Our background spans operations, strategy consulting, and hands-on sales leadership. We bring a multi-lens perspective that most sales-only advisors can't — connecting the commercial strategy to the operational reality of executing it.

Selected Results

We've been where you are. And we know the way forward.

Across PE-backed companies, enterprise consulting engagements, and early-stage org builds, here's a snapshot of what we've helped companies accomplish.

PE-Backed Services Company
Built a full commercial operation — from dispatch to AR — driving a successful strategic exit

Designed and led a 35-person organization spanning sales, dispatch, customer service, insurance partnerships, and accounts receivable at a specialty services company backed by private equity. Drove the commercial strategy that led to a successful exit to a strategic acquirer.

30% YoY revenue growth
+15pp conversion rate lift
−30 days reduction in DSO
Sales Org Build
Took a sales function from zero to a 25-person team across every revenue discipline

Built a full-stack sales organization from concept — including BDR function, Account Executives, Digital Marketing, and a Channel Partnership team. Designed role architecture, hiring process, onboarding programs, and performance frameworks from the ground up.

25 person team built from scratch
4 distinct revenue functions stood up
Medical Device Distributor · $25M
New GTM strategy and sales role redesign drove measurable revenue growth within the year

Leveraged analytics to design a new go-to-market strategy, created new sales roles aligned to customer segments, and built a sales effectiveness KPI dashboard. Facilitated a bespoke rollout workshop for the full sales and executive team.

8% reported revenue increase
New incentive tracking system implemented
Global Medical Device Manufacturer · $30B
Designed and delivered a global sales compensation training program for the executive sales team

Created and facilitated a global training program to align sales executives across regions on incentive compensation strategy, plan mechanics, and performance expectations. Delivered across multiple markets and leadership levels.

Global multi-region rollout
Executive Search Firm · $100M
New GTM strategy and compensation redesign generated multi-million dollar first-year revenue lift

Created a comprehensive go-to-market strategy and redesigned sales compensation plans to better align rep behavior with firm growth objectives. Results were realized in year one.

$MM+ gross revenue increase in year one
Financial Services Software · $2B
Redesigned sales coverage model — net neutral headcount, meaningful revenue upside

Developed a new customer segmentation model and sales coverage strategy that restructured how the sales team was deployed across accounts — achieving revenue growth estimated at 2–3% with no increase in headcount.

2–3% estimated gross revenue increase
Net 0 change in sales headcount
Who We Serve

The right fit matters — for both of us.

We do our best work when we're embedded with companies that are ready to build, not just explore. Here's who we typically partner with.

🌱
Startups & Early-Stage Companies

You've validated product-market fit and you're ready to stop being the only salesperson in the room. We help founders build the first real sales function — from the ground up, the right way.

📈
Mid-Market Growth Companies

You've grown, but growth has outpaced your infrastructure. Territories are unclear, comp plans haven't kept up, and your best reps are figuring things out on their own. We bring the structure that lets you scale.

🏦
PE-Backed Businesses

You need a commercially sophisticated leader who can professionalize revenue operations quickly — someone who understands both the investor expectations and the on-the-ground reality of getting a sales team to perform.

About Bridgepoint

An unusual background. A distinctive edge.

Bridgepoint Sales Advisors was founded on a simple belief: the best results don't come from a presentation — they come from truly knowing the people behind the process.

Our lead advisor brings more than two decades of experience across operational leadership, strategy consulting, and hands-on sales org building. That foundation began with over a decade managing P&L across dozens of high-volume retail locations — learning, at scale, how systems, incentives, and people interact when the stakes are real.

That operational lens carried into sales and revenue work — leading business development at a B2B technology company, spending four years as a management consultant at a global professional services firm working with businesses ranging from $25M distributors to $30B multinationals, and most recently serving as Head of Central Operations at a PE-backed specialty services company through a successful strategic exit.

What we bring to every engagement is rare: the ability to design the strategy and operate within the reality of executing it — with your team, in your market, inside your actual constraints.

We're based in the Chicago area and primarily serve clients across the Midwest, though we work with the right companies wherever they are.

Education
M.B.A. — University of Chicago Booth School of Business
Concentrations: Marketing, Strategic Management, Statistics
Education
B.A., Business Administration — Illinois Wesleyan University
Experience Highlights
20+ Years Across Operations, Consulting & Sales Leadership
Retail operations · B2B tech · Global management consulting · PE-backed services
Industry Depth
B2B SaaS · Medical Devices · Financial Services · Specialty Services · Retail
Geography
Chicago & Midwest-Based
Serving clients regionally and remotely
Let's Work Together

Ready to build something that actually lasts?

The first conversation is a fit check — no pressure, no pitch deck. Just an honest discussion about where you are, where you want to go, and whether we're the right partner to help you get there.