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About True North ITG. Inc.

True North ITG, Inc. is a Healthcare IT managed services company. We serve independent physician practices, specialty groups, regional health systems, and healthcare technology companies across the country. Our work is security-first and compliance-driven — because in healthcare, getting it wrong costs more than money.

We've been doing this for 30 years. We manage complex clinical environments, run cloud migrations that hospitals trust with PHI, and deploy AI-powered operations on our own infrastructure before we ever recommend it to a client. We practice what we preach.

We're growing. We have the brand, the portfolio, the client base, and the pipeline. What we need is a closer — someone who knows how to turn a $200K managed services opportunity into a signed contract, not a stale HubSpot record.

The Role

This is a hunter position. Pure net new business. If your best skill is renewing existing accounts, this is not the right seat.

You will own the full sales cycle — from prospecting into healthcare organizations to closing managed services and cloud contracts in the $50,000 to $500,000+ range. You'll build your own pipeline, work warm referrals from our existing network, and close deals that others leave on the table.

The right person has done this before in Healthcare IT. They know what an MSP actually delivers. They can speak a CIO's language and a CFO's language in the same meeting. They have closed deals where HIPAA, HITRUST, and cloud security were part of the conversation — not an afterthought.

This is not a lead-generation role. This is not an SDR with a VP title. This is a senior closer who builds relationships, navigates complex buying committees, and gets contracts signed.

What You'll Sell

The portfolio is built for the complexity of healthcare IT. You won't be selling commodity services. You'll be selling outcomes — security, uptime, compliance, and transformation.

Core Services

Healthcare Managed IT Services (MSP)

Cloud Hosting & Migration (Azure, DaaS, VDI)

Healthcare Cybersecurity & SOC Services

HIPAA / HITRUST Compliance Programs

AI-Powered IT Operations & Helpdesk

Clinical Data Archiving

Disaster Recovery & Business Continuity

What Success Looks Like

Year 1

• $1.5M closed net new (ramped H2)
• Pipeline of $5M+ built and active
• 4–6 managed services contracts signed
• HubSpot pipeline is current within 7 days

Year 2

• $3M annual quota at full rate
• Avg deal size $100K+
• Consistent $750K/quarter attainment
• Win rate of 30%+ on qualified opps

Beyond

• Path to VP Sales / Sales Leader
• Equity conversation begins
• Team-building opportunity
• Uncapped commission potential

True North's portfolio is built for the complexity of healthcare IT. You won't be selling commodity services. You'll be selling outcomes — security, uptime, compliance, and transformation.

What You'll Do

• Own the full sales cycle from initial outreach through signed contract — no hand-offs, no excuses
• Prospect directly into independent practices, specialty groups, health systems, and healthcare technology companies
• Build and maintain a live, qualified pipeline of $5M+ in HubSpot at all times — with close dates, stages, and next steps that are real
• Close managed services and cloud contracts ranging from $50,000 to $500,000+ in annual contract value
• Navigate complex buying committees — IT, CFO, COO, and clinical leadership in the same deal
• Collaborate with True North's technical team to scope, price, and propose solutions — this is a consultative sale
• Lead discovery conversations that uncover security gaps, compliance exposure, and cloud readiness — not feature demos
• Work referral pipeline from True North's existing client base, partner network, and MDemr channel
• Represent True North at Healthcare IT conferences, regional health system events, and MGMA / HIMSS forums
• Maintain HubSpot records with discipline — close dates within 30 days, stage progression weekly, no dead deals sitting
• Report pipeline status, forecast, and at-risk deals to leadership on a weekly cadence
• Hit $750,000 in closed net new revenue per quarter at full ramp

What You Must Have

Non-negotiable.

• 7+ years of B2B technology sales experience, with at least 3 years selling to healthcare organizations
• Demonstrated track record of closing managed services, cloud, or IT outsourcing contracts — deals over $100K ACV
• Deep understanding of the healthcare buyer: you know what keeps a practice administrator, CIO, and CMO up at night
• HIPAA literacy — you can have a compliance conversation without a lawyer in the room
• Experience selling cloud infrastructure: Azure, hosted desktop (DaaS/VDI), or healthcare cloud environments
• Hunter DNA — you have built pipeline from scratch, not inherited a territory and worked the renewals
• Quota attainment: $1M+ per year in closed net new business for at least 2 of the last 3 years
• CRM discipline: your HubSpot or Salesforce is a real forecast tool, not a graveyard of stale deals
• Ability to travel 20–30% for client meetings, events, and on-site discovery sessions

What Sets the Best Candidates Apart

• Experience at a Healthcare IT MSP, regional VAR, or cloud-first managed services provider
• Existing relationships inside independent physician groups, MSOs, or regional health systems you can call on Day 1
• Familiarity with clinical application hosting: Veradigm (Allscripts), athenaPractice, Cerner, Epic
• Cybersecurity sales experience in healthcare — SOC, EDR, vulnerability management, HITRUST advisory
• Knowledge of healthcare revenue cycle and back-office IT — you understand the difference between a PMS and an EHR
• Experience selling through channel partners or referral networks (health systems, EMR vendors, consultants)
• HIMSS or CHIME network connections
• Experience closing enterprise deals with 6–12 month sales cycles and multiple stakeholders
• Background in clinical data archiving, EMR transitions, or practice acquisition/consolidation IT

Compensation & Benefits

Base Salary: $150,000–$180,000, depending on experience and existing book of business

On-Target Earnings: $300,000–$360,000 at quota ($750K/quarter net new)

Commission: Uncapped. Accelerators kick in above 100% quota attainment

Commission Rate: Tiered on ACV of contracts closed — higher rate on multi-year and larger contracts

Draw Period: 6-month ramp draw while building pipeline. Quota ramps from 25% to 100% over 12 months

Benefits: Medical, dental, vision, 401(k) with match, paid time off

Remote: Fully remote. Travel required 20–30% for client meetings and industry events

Tools Provided: HubSpot CRM, LinkedIn Sales Navigator, full tech stack, marketing support

Why True North

Most MSPs sell commodity IT support. We don't.

True North operates in one of the most complex, regulated, and high-stakes environments in technology: healthcare. Our clients are independent practices and health systems that can't afford downtime, can't afford a breach, and can't afford an IT partner that guesses. They call us because we know their world.

We run AI on our own helpdesk before we recommend it to anyone. We stopped a major Co-Pilot rollout for a health system before the lawyers even knew there was a problem. We've been called in after go-live failures to clean up what the last vendor left behind.

That credibility is what you'll be selling. It's not a pitch deck — it's 30 years of earned authority in a market that punishes bluffs.

What You Get

• A proven portfolio you can sell with confidence
• A CEO who has been in the room with your buyers for 30 years
• Warm referral pipeline from MDemr, channel, and existing clients
• Marketing that generates inbound in healthcare — not generic noise
• Technical pre-sales support that knows healthcare cold
• A company that has never lost a client to a competitor on service quality

What We Expect

• You build real pipeline — no wishful thinking in HubSpot
• You know your numbers cold at any moment
• You advance deals or kill them — nothing sits for 6 months
• You show up at HIMSS, MGMA, and regional events
• You close contracts, not just relationships
• You hit $750K net new per quarter at full ramp

The Bottom Line

Healthcare IT is not a market where generalist sales reps thrive. The buyers are sophisticated. The compliance requirements are real. The deals are complex. The stakes are high.

If you have 7+ years of selling managed IT or cloud to healthcare organizations, a track record of closing contracts over $100K, and the hunger to build something — we want to talk.

If you're looking for a territory to coast on, this isn't it. True North is a company that earns every client. We need a sales leader who earns every contract.

True North IT Group is an equal opportunity employer. We evaluate candidates based on one thing: the ability to close Healthcare IT contracts at scale.

At True North ITG, Inc., we're at the forefront of Healthcare IT evolution, leveraging technology intelligently to enhance client experiences. As a Managed Services Provider (MSP), we're dedicated to making IT operations smarter, more streamlined, and ultimately, more successful.

Our team is comprised of dedicated individuals driven by the desire to make a tangible impact. If you're an ambitious self-starter with an entrepreneurial mindset, who thrives in a collaborative environment alongside exceptional colleagues, let's connect!