Fast Facts

Apptegy is seeking a Head of Product Strategy and Operations to drive product strategy and operational excellence, serving as the Chief of Staff to the CPTO and leading cross-functional initiatives to enhance school communications.

Responsibilities: Key responsibilities include formulating product strategy, running operational rhythms, building product health dashboards, and leading a Product Ops team for effective execution.

Skills: Candidates should have proficiency in product strategy, operations, data fluency, executive-level communication, and experience with B2B SaaS environments.

Qualifications: A Bachelor’s degree is required, with an MBA preferred and 10+ years of relevant experience in product strategy and operations in a multi-product SaaS setting.

Location: This position is based in Chicago, Illinois, USA.

Compensation: $140000 - $250000 / Annually

Who We Are

At Apptegy, we are more than a SaaS company; we are partners dedicated to transforming how schools communicate and shape the future of education. Your work here will directly empower districts to share their stories, engage their communities, and celebrate student success.

We're a team of thoughtful, high-performing individuals committed to making a tangible impact. If you're looking for a dynamic environment where you'll be supported with exceptional mentorship and resources to grow your career, come build with us.

The Role

You will be the operating engine for Product & Engineering — turning strategy into outcomes. You’ll connect our vision to what ships: working with the team to set a clear product strategy, and then running a crisp operating cadence, and turning data and customer signal into the right portfolio bets. Day to day, you’ll make it easier for teams to do their best work — and you’ll see the impact in faster delivery, cleaner launches, and products that meaningfully serve schools.

You’ll also serve as Chief of Staff to the CPTO, keeping leaders aligned, decisions unblocked, and our roadmap tied to business results. If you love simplifying complexity, telling a clear story with numbers, and rallying product, engineering, and go-to-market around measurable goals, this role is for you.

What you’ll do

• Work with the CPTO and the product & engineering leadership team to form the product strategy, and then facilitate portfolio planning, quarterly investment trade-offs, and outcome measurement via OKRs
• Run the PD&E operating rhythm (QBRs/MBRs, release governance, risk/dependency reviews, post-launch impact)
• Build unified product health and ROI dashboards with Data and Finance (adoption, engagement, NRR impact, NPS, cost to serve)
• Translate research, Sales/CS insights, and support data into clear bets, experiments, and decision memos
• Orchestrate cross-functional launch readiness with GTM, CS, Security, and Legal; tighten handoffs from discovery to adoption
• Serve as Chief of Staff to the CPTO (staff cadence, offsites, ELT/board materials, tracking strategic initiatives)
• Lead and grow a small but experienced Product Ops team (3 existing team members); own the product tooling stack and data quality standards

What you’ll bring

• Bachelor’s degree required; MBA or related advanced degree preferred
• 10+ years in B2B SaaS across product strategy/operations/management, including multi-product or platform scope
• Proven portfolio and investment planning with quantified outcomes (e.g., NRR, adoption, cost to serve)
• Mastery of operating cadence (OKRs, QBRs/MBRs, release governance, risk/dependency management)
• Executive-level communication: clear narratives and decision memos for ELT/board tied to metrics
• Strong data fluency: KPI frameworks, ROI dashboards with Finance/Data, experimentation literacy
• Cross-functional execution with GTM and CS from discovery through launch and post-launch measurement
• Ability to simplify processes, drive adoption, and maintain a high bar on execution quality
• Proficiency with roadmap/work management and product analytics tools; comfortable querying or partnering on data

What makes you stand out

• You’ve owned a portfolio with clear ROI, showing how trade-offs improved NRR, adoption, and cost to serve.
• You’ve acted as a true Chief of Staff to a product/tech leader—driving cadence, decisions, and board-level storytelling.
• You turn noisy data into crisp narratives and dashboards leaders actually use.
• You’ve simplified a complex operating model and increased speed without adding bureaucracy.
• You’ve launched cross-functional initiatives that stuck—GTM alignment, launch readiness, and measurable post-launch impact.
• You’ve led distributed teams across the Americas and understand the practical implications of country-specific processes.
• You’re comfortable shaping AI-era product operations (evaluation frameworks, governance, and responsible rollout).

$140,000 - $250,000 a year

Why Apptegy

Join a team that’s committed to your success. At Apptegy, we’re passionate about creating an environment where you can do your best work and find true fulfillment. We believe in investing in our people—both professionally and personally—because your well-being drives our collective impact.

Comprehensive medical, dental, vision, and life insurance coverage

Retirement 401(k) with employer match

Health Savings Accounts (HSA) and Flexible Spending Accounts (FSAs)

Mental Health Reimbursement

Unlimited paid time off, including seasonal (December) company-wide time off

Paid parental and medical leave

Equal Opportunity Employer

Apptegy is an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, gender expression, national origin, age, protected veteran or disabled status, or genetic information.