Chief Technology Officer

Milwaukee, WI
Full Time
Senior Executive

Be the Tech Visionary Behind a High-Performing MSP’s Next Chapter

At River Run, we don’t just support technology—we power businesses with it. For 32 years, we've been redefining what exceptional IT service looks like, and now, we’re writing our most ambitious chapter yet: aggressive growth, next-level innovation, and client experiences that wow.

We’re looking for a Chief Technology Officer (CTO) who is part strategist, part operator, and all-in on building something meaningful. You’ll lead and scale our technical services division, shape our future offerings, and inspire a 70+ person team to do their best work. If you’re a seasoned MSP leader with deep cyber security expertise, a track record of operational excellence, and a relentless drive to deliver results, this is your moment.

🔍 What You’ll Do

Set Vision & Drive Strategy

  • Define and own the technical vision that aligns with River Run’s bold growth goals.

  • Build out a scalable, resilient tech services structure across service delivery, cybersecurity, and project execution.

  • Recommend and implement cutting-edge technologies and partnerships that future-proof our offerings.

Lead a High-Performance Team

  • Mentor and develop technical leaders to build strong, engaged teams that thrive on accountability and innovation.

  • Foster a culture of continuous improvement using real-time client feedback to fuel evolution.

  • Inspire a team-first mentality where excellence and personal growth go hand in hand.

Deliver Operational Excellence

  • Own the department’s success—from process improvement and documentation to utilization, capacity, and quality of service.

  • Drive automation, standardization, and proactive security practices that keep us ahead of the curve.

  • Ensure consistency, clarity, and excellence through strong SOPs and ticketing standards.

Strengthen Client Partnerships

  • Ensure every tech interaction is a positive client experience.

  • Collaborate with account management and sales to drive technical trust and retention.

  • Present with confidence to business and executive stakeholders.

✅ What You Bring

  • 4+ years of executive leadership in an MSP 

  • A proven track record of building scalable systems and teams in growth-stage companies.

  • Mastery of MSP tools and standards (PSA, RMM, ITIL, NIST, etc.).

  • Deep technical chops across infrastructure, cloud (Azure/AWS), cybersecurity frameworks (SOC 2, CMMC), and emerging tech (AI, automation).

  • Strong business acumen—you connect tech decisions to bottom-line results.

  • Executive presence and the ability to inspire trust and action from the C-suite to frontline techs

🌟 Why River Run?

  • Join a thriving, 32-year-old MSP with serious momentum and a startup energy.

  • Work with a passionate, driven team that actually likes showing up every day.

  • Your leadership will directly shape our clients, our company, and our culture.

  • Competitive compensation, profit sharing, and full benefits package.

  • An opportunity to leave your fingerprint on something that’s growing—and growing fast.

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