Your revenueproblemhas a name.it's not enough.
Sightline builds and fixes commercial organizations — fast, without the full-time hire.
AI-powered commercial operations, founded by Dan Cunningham — 22 years inside Pfizer, Bayer, Siemens, Stryker, Hill-Rom, and Bioventus.
Founded by Dan Cunningham · Fractional CRO · Chicago, IL
Backed by leadership experience from
Key partnerships & clients
Most organizationsdon't have astrategy problem.They have aleadership gap.
Dan Cunningham is the founder of Sightline. He's spent 22 years inside the most demanding commercial environments in healthcare — Pfizer, Bayer, Siemens, Stryker, Hill-Rom, and Bioventus— and the story is almost always the same. The market opportunity is real. The team has potential. But there's no one at the top who can own the revenue function, install the right infrastructure, and make the whole machine move.
Sightline exists to fix that. Dan steps into organizations at critical inflection points — scaling, turning around, or breaking through plateaus— and builds the commercial clarity that turns good companies into exceptional ones. The methodology is documented. The playbook is proven. And increasingly, two of Sightline's three service tiers don't require Dan in the room to deliver.
The organizations Sightline partners with build teams where AI handles 80% of the administrative and analytical burden — so people can do what only great people can do: build real relationships, make sharp decisions, and close business that matters.
Sightline's Mandate
“Not just stabilize. Not just optimize. Genuinely accelerate — or we're not the right call.”
Track Record
Roles where quota was missed.
20+ years. Every market condition. Every economic cycle. Not once.
Consistency
Consistent growth across every market condition.
Expansion markets. Downturns. Pandemic years. Post-merger chaos. The external environment has never been the determining factor. Execution always is — and execution is what I bring.
Organizational Impact
Commercial infrastructure, not just headcount.
I don't hire people and hand them a quota. I install the process, culture, accountability, and AI operating model that makes the entire revenue organization perform — and keeps performing after I'm gone.
Sightline · AI Commercial Operations
Sightline's methodology targets 80% reduction in administrative workload — so your team spends their time selling, not reporting. Two of our three service tiers are fully deliverable without Dan in the room. That's how a founder-led firm becomes a scalable company.
What Sightlinebrings to everyengagement
Four capabilities. Proven across 9 commercial organizations. Documented in results — not PowerPoints.
Turnaround & Revenue Architecture
Sightline walks into broken — and leaves it growing.
Most fractional executives advise. Sightline installs. New structure, new process, new accountability — all while keeping revenue moving. We've rebuilt organizations up to 85% new headcount in Year 1 and still grew 40%+ YOY. We don't just diagnose the problem. We fix it.
Enterprise & Distribution Dealmaking
If the deal is stuck, we unstick it.
IDNs, GPOs, health systems, national distributors — Sightline has negotiated at the highest levels of complex, multi-stakeholder healthcare commerce. We know where deals die, how they get restarted, and how to close at the C-suite level. 250+ distribution partners managed. Deals that became company records.
Remote Revenue Org Leadership
Geography is not an excuse Sightline accepts.
Sightline has built and led distributed teams across fully remote environments — and outperformed quota in every single one. Culture, accountability, and momentum without a shared office. In today's commercial landscape, this is the edge, not the exception.
AI-Driven Commercial Operations
Your team is doing manually what AI should own.
Sightline doesn't just talk about AI transformation — we've deployed it inside real commercial organizations and watched revenue follow. Our operating model eliminates 80% of administrative workload, accelerates onboarding, and enables real-time performance coaching at scale. This is the methodology that powers all three service tiers.
One methodology.Three waysto engageSightline.
A buyer who starts with the AI Commercial Audit experiences the same methodology that powers every Sightline engagement. The staircase isn't a sales funnel — it's a continuity of thinking. Start anywhere, scale as needed.
Hiring a full-time CRO takes 6–9 months and $400K+. Your deals won't wait.
Your team burns 80% of their day on tasks AI should already be handling.
Your competitors are closing IDN contracts while you're still building process.
Start with the $500 AI Commercial Audit. Understand the problem before committing to a solution.
Scale into implementation or Fractional CRO when — and only when — you're ready.
Productized · Fixed fee · No long-term commitment required
Heads up: I take on a limited number of engagements at a time to protect the quality of every client relationship. If you're reading this, a spot is currently open.
Every weekyou wait ispipeline youwon't get back.
I respond to every inquiry personally — no assistant, no auto-reply, no sales process. If you're thinking about your commercial challenges, that's enough reason to reach out. The first conversation is free, pressure-free, and built around your situation — not our pitch.If Sightline isn't the right fit, Dan will tell you that too.
Phone
708.288.3599Location
Chicago, IL — serving clients nationally
My Commitment To You
No pitch. No pressure.
Just a real conversation.
In 30 minutes I'll tell you exactly where your revenue operation is leaking, what the fastest path to fixing it looks like, and whether I'm the right person to lead it. You'll walk away with clarity regardless of what you decide.
Response within 1 business day — every inquiry answered personally by Dan Cunningham, Sightline founder.
Limited availability: I take on a select number of engagements at a time. Spots are currently open — but that changes without notice.