Lead product strategy execution and operations for Product & Engineering: set portfolio strategy, run operating cadence (OKRs/QBRs/MBRs), build ROI and product health dashboards, translate customer and research signals into prioritized bets, orchestrate cross-functional launches, serve as Chief of Staff to the CPTO, and grow a small Product Ops team to improve delivery speed, launch quality, and measurable product outcomes.
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).
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.
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With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
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