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Salary: USD 133,000 - 150,000 / annual
Rundoo is a venture-backed B2B SaaS company (Series B, $48M raised) modernizing technology for independent supply stores—hardware stores, nurseries, and building-material retailers. Over 200,000 such stores across North America currently rely on outdated on-premises systems; Rundoo is live in 500+ stores and integrated with 20+ industry partners.
You will lead the Implementation team as Manager, Implementation, owning all aspects of customer go-live and post-sale delivery. This is a hands-on leadership role where you set strategy, coach Implementation Managers, and drive measurable commercial outcomes tied to ARR.
Key responsibilities:
- Own team performance against ARR and go-live targets, including through periods of growth and ramp
- Build a high-accountability culture: set clear expectations, celebrate wins, address misses directly, and ensure ownership stays with individual IMs
- Design and maintain a rules-based resource allocation process to avoid over/under-capacity
- Run operating cadence: pipeline reviews, forecasting meetings, no-push reviews, training, and call coaching
- Create a simple, memorable, client-centered implementation process with clear, customer-verifiable exit criteria at each stage
- Build a repeatable escalation playbook so IMs can resolve common issues independently
- Develop an ARR forecasting model that predicts outcomes within ~25% accuracy
- Coach the team with direct, actionable feedback grounded in customer and business impact
- Partner cross-functionally with Sales, Product, and Customer Experience to improve handoffs and shorten time-to-live
Within your first several months, success means: establishing a clear operating cadence with visibility into team performance; helping the team achieve at least 80% quota with broadly distributed attainment (not reliant on one or two top performers); implementing a branded, verifiable implementation process; building an escalation system that empowers IMs; producing a reliable ARR forecast; and creating a culture where expectations are clear, strong effort is celebrated, and misses drive learning and accountability.
The team currently includes five Implementation Managers with backgrounds in food tech, legal tech SaaS, agriculture, and operations startups. You will report to GTM leadership.
REQUIREMENTS:
- Chicago-based and willing to work in office minimum 4 days/week
- High-accountability leadership style paired with genuine commitment to supporting your team
- Experience leading an implementation, onboarding, professional services, customer success, or other post-sale team with a measurable delivery or revenue target
- Track record of helping a team consistently hit its number—not relying on one or two top performers
- Strong operating discipline: pipeline management, forecasting, resource allocation, performance management
- Excellent coaching skills; ability to deliver feedback that is both direct and actionable
- Strong judgment under pressure; ability to distinguish between issues the team should solve and those requiring escalation
- Clear written and verbal communication across frontline team members, executives, and cross-functional partners
- Comfort operating in a fast-moving startup where processes must be built, simplified, and reinforced as the company scales
BONUS:
- Experience leading implementation for B2B SaaS, payments, ERP, point-of-sale, or other workflow-critical software
- Experience serving independent retailers, building-material suppliers, or operationally complex businesses
- Experience tying implementation milestones to ARR recognition or activation
- History of building memorable, scalable playbooks that teams actually use
- Experience improving forecasting accuracy and capacity planning for a growing delivery organization
- Energized by turning a good team into a high-performance team
