Implementation project manager Jobs in Chicago, IL

Manager, Implementation at Rundoo

We're hiring a Manager, Implementation to lead the team responsible for getting every new Rundoo customer live and successful. You'll own implementation outcomes across the business: team attainment, resource allocation, operating cadence, process design, escalation, and forecasting.

This is a hands-on leadership role for someone who sees implementation as a commercial discipline. You'll set clear expectations, coach Implementation Managers to own customer outcomes, and build a culture where winning is celebrated and accountability is non-negotiable. You'll report to our GTM leadership and partner closely with Sales, Product, and Customer Experience.

Your mandate is simple: help the team reliably hit its number while delivering a clear, client-centered path to go-live.

What You'll Do as Manager, Implementation at Rundoo

• Own team performance: Lead the Implementation team to consistently achieve its ARR and go-live goals, including through periods of team growth and ramp

• Build a culture of winning and accountability: Set ambitious but realistic expectations, celebrate strong performance, address misses directly, and ensure ownership stays with the Implementation Manager

• Allocate resources: Create and maintain a rules-based resource allocation process, ensuring we don't have over or under capacity IMs

• Run the operating cadence: Lead Pipeline Reviews, "Hit the Number" meetings, no-push reviews, ongoing training, and call coaching

• Design and enforce a client-centered implementation process: Create simple, memorable stages with clear exit criteria verified through customer actionnot just completion of internal tasks

• Create a repeatable escalation playbook: Equip Implementation Managers to resolve common challenges independently and escalate the right issues at the right time, without turning the manager into the default hero IC

• Improve forecasting: Build an ARR forecasting model that gives the company a reliable view of expected implementation outcomes and supports better resource planning

• Coach the team: Give clear, actionable feedback grounded in customer and business impact; use thoughtful questioning to help team members identify and own their next steps

• Partner cross-functionally: Work with Sales, Product, and Customer Experience to improve handoffs, resolve systemic blockers, and shorten time to live

Requirements

• Chicago-based and excited to work in an office at minimum 4 days/week

• A high-accountability leadership style paired with a 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

• A track record of helping a team consistently hit its numbernot relying on one or two top performers

• Strong operating discipline, including pipeline management, forecasting, resource allocation, and performance management

• Excellent coaching skills, with the ability to deliver feedback that is both direct and actionable

• Strong judgment under pressure and the ability to distinguish between issues the team should solve and issues that require 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 Points

• Experience leading implementation for B2B SaaS, payments, ERP, point-of-sale, or other workflow-critical software

• Experience serving independent retailers, building-material suppliers, or similarly operationally complex businesses

• Experience tying implementation milestones to ARR recognition, activation, or other commercial outcomes

• A history of building memorable, scalable playbooks that teams actually use

• Experience improving forecasting accuracy and capacity planning for a growing delivery organization

• You are energized by turning a good team into a high-performance team

What Success Looks Like

Within your first several months, we expect you to:

• Establish a clear operating cadence and create visibility into team performance

• Help the team achieve at least 80% of its aggregate quota through broadly distributed attainment

• Implement a simple, branded, client-centered process with verifiable exit criteria for every stage

• Build an escalation system that enables Implementation Managers to solve more issues independently

• Produce an ARR forecast that predicts outcomes within approximately 25%

• Create a culture where expectations are clear, strong effort and results are celebrated, and misses lead to learning and accountability

Interview Process

1. Recruiter screen (30 minutes) Discuss your background, leadership experience, and interest in Rundoo. If all goes well, we'll send you a short take-home exercise to complete.

2. First round (30 minutes) Meet with the hiring manager and review a short take-home exercise: design a simple, memorable implementation process with clear stages and customer-verifiable exit criteria

3. On-site working session (approximately 1.5 hours) Coach two implementation calls and lead a mock pipeline review using a sample go-live calendar and team pipelines

4. Team lunch (30 minutes) Meet members of the Rundoo team

5. Founder Chat (15 minutes) Final conversation with our CEO, Nick

Compensation

• Base salary: $133K

• Target variable compensation: $17K

• Equity: $26,000 vesting over four years

Benefits

• Full medical, dental, and vision coverage (100% of premiums for you, 50% for dependents)

• Life insurance

• 401(k) with Betterment

• Unlimited PTO with 10 company-paid holidays

• Daily team lunches for those in office

• Learning materials and audiobook subscriptions