Senior Technical Program Manager (Hybrid)
About The Position
The Senior Technical Program Manager at Rewards Network owns the planning, governance, and delivery of the company's most complex, strategic programs — including large-scale product transformations on our consumer- and restaurant-facing sides of the business, major product modernization initiatives (from discovery through launch), large-scale partner and restaurant onboarding programs, new strategic partner and payments integrations, and core payments infrastructure upgrades and migrations. Each of these spans multiple concurrent workstreams across Product, Engineering, Data, Partner Management, Marketing, and Operations. This role owns the end-to-end timeline, success, and delivery health of that program portfolio — from Conception through launch — establishing the operating rhythm and managing cross-program dependencies, risk, and stakeholder communication so Rewards Network's highest-priority initiatives land on time, meet a standard of greatness, and align with business objectives. This is an embedded owner into the cross-functional team: someone senior enough to operate without handholding, deep enough in the details of the work to know why each program matters (not just its next milestone), and comfortable reporting credibly in both directions — upward (to executives and senior leaders) with clean, balanced, actionable updates, and outward (to Partners, Ops, Marketing, and Engineering) to ensure alignment. This role reports directly to the Senior Director of Product and is an experienced individual contributor role for someone who thrives at the intersection of rigorous program governance and cross-functional influence at the executive level. This is a hybrid position that requires in office presence 3 days a week (Tuesday-Thursday) in Chicago.
Requirements
- Bachelor's degree in Business, Engineering, Computer Science, or a related field.
- 7-10 years of technical program or project management experience delivering software/technology initiatives in a SaaS, B2B, B2C, or B2B2C environment, including experience managing a portfolio of related, concurrent programs.
- Demonstrated experience leading a portfolio of multiple concurrent, related programs from inception to launch, with enough technical fluency to engage credibly with Engineering on architecture, sequencing, and risk.
- Experience working with Agile delivery teams (Scrum, Kanban, or hybrid).
- Experience presenting program-level status to executives and senior-leaders.
- Demonstrated ability to ramp quickly into ambiguous, in-flight programs and operate independently within days or weeks, not months.
- Strong program and project management fundamentals: scope definition, scheduling, cross-program dependency management, identifying risks, risk management, and change control.
- Excellent ability to translate ambiguous business goals into structured, actionable plans with clear milestones and accountability.
- Proven experience leading cross-functional programs (engineering, design, product, marketing, partner management, operations) without direct authority.
- Operates as an embedded owner, not a meeting scheduler or status relay — brings a point of view on risk and sequencing rather than simply passing along what others report.
- Comfortable partnering with Product Marketing and Marketing on go-to-market execution — translating an agreed positioning and messaging strategy into a coordinated, cross-functional launch plan, timeline, and readiness checklist.
- Proficiency with program and project management and collaboration tools: JIRA, Confluence, Asana, Miro; comfort with reporting tools and dashboards (e.g., advanced JIRA, Tableau, or similar). Experience designing and running a program governance model — steering committees, working-team cadences, and demo/review rhythms — that scales with a program's complexity.
- Strong analytical skills and the ability to use data to inform planning, identify bottlenecks, and measure delivery health.
- World-class written and verbal communication skills; ability to tailor messaging from individual contributors up to executive leadership.
- Calm under pressure with strong stakeholder management, negotiation, and conflict resolution skills.
- AI-native and proficient with modern AI tools (e.g., ChatGPT, Glean, Claude) to accelerate day-to-day program management — drafting plans and status updates, synthesizing data across systems, and surfacing risks faster — with a mindset of continuously adopting new AI-enabled workflows as they emerge.
- Ability to manage multiple, complex, competing priorities in a fast-paced, ambiguous environment.
Nice To Haves
- PMP, PgMP, CSM, PMI-ACP or equivalent program/project management certification.
- Experience in FinTech, MarTech, restaurant, dining, hospitality, or loyalty/rewards industries.
- Experience coordinating with external partners (e.g., loyalty programs, integration partners, vendors) on joint roadmaps and delivery commitments.
- Experience coordinating product launches or go-to-market execution in partnership with Product Marketing or Marketing teams.
- Experience managing data, analytics, or AI/ML-driven product initiatives.
Responsibilities
- Own end-to-end program management for Rewards Network's most complex, cross-functional strategic initiatives — spanning platform transformations, product modernization efforts, large-scale partner and merchant onboarding, new partner and payments integrations, and core payments infrastructure upgrades — often managing several concurrently.
- Define and maintain program plans, timelines, milestones, and cross-program dependency maps; drive accountability against committed dates and quality bars.
- Proactively identify, track, and mitigate risks and issues; escalate appropriately and recommend trade-offs when scope, schedule, or resources require rebalancing.
- Work with Product leadership to ensure the right work is sequenced against available resources. Establish and run the governance operating model — steering committees, working-team cadences, and review rhythms — to keep each program's health visible without active leadership involvement.
- Own program-level reporting and status communication to executives, senior leadership, and key stakeholders; translate complex delivery details across multiple concurrent programs into simple, clear, decision-ready summaries.
- Manage cross-program dependencies with internal partners and external integrations (e.g., loyalty program partners); ensure alignment on requirements, timelines, and acceptance criteria across every program in the portfolio.
- Own the cross-functional execution of product launches and go-to-market plans: coordinate readiness, dependencies, timing, and stakeholder alignment across Product, Engineering, Marketing, Sales, Legal, Finance, and Partner Management. Partner closely with Marketing on positioning and messaging, but owns the plan, the timeline, and an on-time, successful delivery.
- Serve as the primary point of contact and connective tissue for cross-functional programs — this includes applying pressure (or escalation) to other leaders as needed to keep programs on-track.
- Continuously improve program management practices, tools, templates, and governance processes, including eliciting feedback on how we can continue to improve them.
- Leverage AI tools and workflows to increase program management velocity and quality — accelerating status synthesis, risk analysis, and plan generation — and model AI-native practices for the broader cross-functional team.
- Champion a culture of clear ownership, transparent communication, and continuous improvement across the organization.
Benefits
- Comprehensive benefits package
- Competitive Time Off Benefits: including flexible PTO, 11 company holidays, and parental leave.
- Generous dining reimbursement when you dine with our restaurant clients
- 401(k) plan with a company match
- Two medical plan options- Standard PPO or High Deductible Health Plan (HSA with company match for HDHP participants)
- Partnership with Rx n Go, offering certain prescriptions for free
- Two dental plan options and a vision plan
- Flexible Spending Accounts and a pre-tax commuter benefit program
- Accident, Critical Illness, and Hospital Indemnity Insurance Plans
- Short Term and Long Term disability
- Company-paid life insurance and AD&D insurance, supplemental employee, spouse, and child life insurance
- Employee Life Assistance Program
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What This Job Offers
Job Type
Full-time
Career Level
Senior
