OpenSesame · 21 hours ago
Head of Workforce Reinvention
United States
Full-time
Remote
Director/Executive
$180K/yr - $240K/yrOpenSesame is a company focused on reinventing how people work in an AI world. The Head of Workforce Reinvention will lead efforts to optimize workflows, automate tasks, and integrate AI into daily operations, aiming for significant business outcomes and employee satisfaction.
EdTechEducationVirtual Workforce
Responsibilities
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
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
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
Qualification
Required
Experience in leading teams focused on AI and automation initiatives
Proven track record of delivering measurable business outcomes
Ability to assess and formalize roles within a team
Experience in auditing workflows to identify automation opportunities
Skills in defining success measures linking productivity gains to business outcomes
Experience in operationalizing processes for deploying AI use cases
Ability to drive functional adoption of AI tools across multiple functions
Experience in hiring or redeploying talent into key operational roles
Skills in quantifying ROI from automation and AI initiatives
Experience in institutionalizing AI-driven work redesign in organizational planning
Ability to implement systems that enhance decision-making speed
Experience in creating training programs for employee engagement with AI tools
Ability to demonstrate links between workforce reinvention and business growth
Benefits
Professional development
ISOs
Health insurance
401(k) matching
Paid time off
Company
OpenSesame
OpenSesame is an e-learning company that provides online training courses for businesses and employees.
Founded in 2011
201-500 employees
Funding
Current Stage
Late StageTotal Funding
$97MKey Investors
JMI EquityFTV CapitalAltos Ventures
2021-07-22Series D· $50M
2019-05-28Series C· $28M
2016-09-27Series B· $9M
Leadership Team
Don Spear
CEO
Joshua Blank
President (Co-Founder)
Recent News
Company data provided by crunchbase