Enterprise Sales Director Jobs in Chicago, IL

About the Role

The Managing Director is the accountable leader for the end-to-end success of a significant program for a strategic customer. Reporting directly to the CCO, this role owns the plan, the people, the customer relationship, and the outcomes from kickoff through go-live and into Phase II and beyond. This is a high-visibility, high-stakes assignment requiring a seasoned operator who can run a complex, multi-workstream program while simultaneously managing a strategic customer relationship.

Program Leadership

• Serve as the single point of accountability from the POC to full deployment and beyond.
• Drive and govern the master project plan across: Onboarding & Configuration, Training & Enablement, Data Migration, Integration, Rollout Execution, Support, and Reporting.
• Chair weekly program stand-ups, steering committee sessions, and executive check-ins.
• Own risk identification, escalation, and resolution.

Customer Relationship

• Act as the primary executive-level contact for the strategic customer stakeholders throughout the engagement.
• Build trust and alignment with project sponsors, operations leads, and office champions.
• Navigate competing priorities, stakeholder ambiguity, and scope discussions with clarity and confidence.
• Represent Karbon's capabilities, roadmap, and commitment with credibility at every level of the customer's organization.

Team Leadership

• Lead and coordinate a cross-functional Karbon team including: Project Management, Implementation, CS, Training, and Support, with collaboration across Product and Engineering.
• Ensure clear role ownership and handoffs across the multi-office implementation for the POC and all elements of Phase II.
• Identify and resolve resource gaps as the program scales through the June–August high-volume rollout window for the POC and Phase II.

Delivery & Outcomes

• Deliver Go-Live for all offices by the target date, with users trained, data migrated, and integrations validated and converted to Phase II.
• Maintain a live risk register and ensure confidence levels across nine identified program risks remain within acceptable thresholds.
• Drive post-go-live health reporting through Fall 2026, producing the POC wrap-up deliverable for executive review.
• Define what POC success looks like and position the engagement for conversion to a full commercial deployment.

About You!

Required

• 10+ years of experience leading complex enterprise SaaS implementations or customer success programs, with P&L or program-level accountability.
• Demonstrated success managing multi-workstream deployments with 100+ end-user locations, tight deadlines, and senior customer stakeholders.
• Strong command of project governance: risk management, dependency tracking, milestone reporting, and executive communication.
• Experience directly leading and managing cross-functional teams, with full people management authority over implementation, CS, training, and support functions.
• Track record of navigating ambiguous, high-stakes situations and making sound decisions under pressure.
• Exceptional communication skills - equally effective in a steering committee with a strategic customer and an internal team stand-up.

Preferred

• Background in practice management, accounting, or professional services technology.
• Familiarity with Karbon or comparable workflow/work management platforms.
• Experience with enterprise rollouts involving custom integrations and multi-tenant architectures.
• Prior experience with large franchise networks or tax/accounting industry clients.

This is a rare opportunity to lead one of Karbon's most consequential customer programs - one that will define how we scale into enterprise-tier deployments. The Managing Director, Strategic Account will have direct visibility with the CCO, Sales executives, CEO and program ownership as well as the chance to build something that lasts. If you thrive in complexity, lead through ambiguity, and want your work to leave a mark, this role is for you.

Why Work at Karbon?

• Gain global experience across Australia, New Zealand, UK, and Canada
• Strong benefits package including:
• • Flexible Time Off with an encouraged 4 weeks use per year
  • Company paid medical for you and eligible spouse/partner and dependents
  • Paid dental and vision and eligible spouse/partner and dependents
  • 401(k) with company matching
  • Flexible Spending Account
  • Up to 8 weeks paid parental leave
  • Work-from-home stipend
• Work with (and learn from) an experienced, high-performing team
• A collaborative, team-oriented culture that embraces diversity, invests in development and provides consistent feedback
• Be part of a fast-growing company that firmly believes in promoting high performers from within