Head of Workforce Reinvention

About OpenSesame

While it appears to most people that we just sell training courses (over 50,000 of them), what we really offer is the opportunity for companies and our own team to reinvent how people work in an AI world.

OpenSesame has already begun this transformation. A small, high-performing internal team is actively pioneering ways to optimize workflows, automate routine tasks, and integrate AI into daily operations. The Head of Workforce Reinvention will now lead, expand, and scale that effort, turning promising pilots into high-impact company-wide results.

This role will oversee the strategy, team, and systems that enable every function at OpenSesame to operate faster, smarter, and with greater joy. It’s about helping people spend more time on meaningful, creative work while driving measurable business outcomes.

Ultimately, success will be defined by achieving 20%+ ARR growth without proportional headcount and expense growth while increasing employee satisfaction as rote administrative work is completed by AI and AI helps drive new, creative solutions.

Performance Objectives

Phase 1: Strengthen and Expand the Foundation (0–6 Months)

• Elevate the Existing Team: Assess current AI and automation initiatives, formalize roles, and strengthen the core Reinvention Team’s charter and structure.
• Build the Reinvention Blueprint: Audit team and cross-functional workflows to identify 25+ automation and augmentation opportunities with tangible business impact.
• Establish Clear Metrics: Define success measures linking time saved, productivity gains, quality metrics improvements, and employee sentiment to top-line outcomes.
• Showcase Early Wins: Partner with existing pilots to highlight internal success stories that inspire confidence and build desire for reinvention projects in every team.

Phase 2: Scale and Systematize Impact (6–12 Months)

• Operationalize the Reinvention Playbook: Standardize processes for identifying, testing, and deploying automation and AI use cases across teams.
• Drive Functional Adoption: Embed AI tools and agents into 3+ major functions (Sales, Marketing, Customer Success) to cut administrative effort by 25% or improve quality by 50%.
• Expand the Team Thoughtfully: Hire or redeploy top talent into key AI operations, automation, and change management roles to scale capacity.
• Quantify ROI: Deliver measurable outcomes that demonstrate at least 10x return on investment in time savings, reduced costs, improved quality, or accelerated revenue cycles.

Phase 3: Redefine the Operating Model (12–18 Months)

• Institutionalize Reinvention: Make AI-driven work redesign part of every manager’s and team’s planning process.
• Transform Workflows: Implement systems that reduce decision latency and increase execution speed by 30–50%.
• Document and Teach: Create an internal “Reinvention Academy” that trains every employee to confidently use AI tools and contribute new automation ideas.
• Show Company-Wide Impact: Demonstrate clear links between workforce reinvention, top-line growth, and improved employee engagement scores.

What Success Looks Like

• The Reinvention Team is recognized as a force multiplier across OpenSesame — small, nimble, and highly applauded by every function.
• Workflows are redesigned to eliminate waste and empower creativity, saving thousands of hours per quarter and improving quality.
• Employees report higher satisfaction and energy, doing less busywork and more meaningful work.
• AI-driven reinvention becomes a core part of OpenSesame’s culture and brand — individuals and teams continuously find, develop, and deploy new AI tools and methodologies..
• The Company achieves 20%+ ARR growth, improves quality metrics, and reduces expenses as a percentage of revenues.

Location: This position can be based anywhere in the US. We operate as a remote-first company and invest in all-company in-person meetings several times a year. 

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, but we're highly selective about who we hire. We don't focus on typical job requirements; instead, we're interested in specific examples from your past experiences. All positions can be based anywhere in the US, and require up to 15 days of travel per year, with senior management and leadership teams requiring up to 35 days.

Compensation: The annual salary range for this role is $180,000–$240,000, depending on experience. At OpenSesame, we offer a comprehensive benefits package to employees upon hire, including professional development, ISOs, health insurance, 401(k) matching, and paid time off. We carefully consider a wide range of compensation factors, relying on market data to determine compensation and consider your specific job family, background, skills, and experience. We prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals.

Equal Employment Opportunity: OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process. 

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance.

CPRA (California Candidates): When you submit your application, OpenSesame may collect and use your personal information in accordance with our privacy policy and the CPRA. This may include personal details and employment history, and will only be used for employment-related purposes. We may share this information with third-party service providers, but we will not sell it to third parties. If you have any questions or concerns, please contact us, and for more information on your rights under the CPRA, refer to our privacy policy or the California Attorney General's website.

We Care About Your Security: We’ve been made aware of a phishing scam involving individuals impersonating OpenSesame recruiters. All legitimate communication from our team will come from @opensesame.com email addresses. If you receive a suspicious message, please contact us directly at [email protected]. Your security matters to us — thank you for staying vigilant