Director of Technical Program Management

We’re Jiffy. We launched over a decade ago with a simple mission: use tech to combine an unparalleled level of customer service with the fastest delivery in the blank apparel, direct-to-film transfer, and custom apparel industries.

We’re more than a T-Shirt company; we’re a support system for the creator + creator economy, home hobbyist, the small business owner, and more. Today, we help millions of small businesses build their vision from scratch. And we’re hiring!

The Director / Senior Manager of Program Management will own cross-functional technical programs that directly impact business outcomes. This role is for someone who can thread alignment across engineering, marketing, product, and business leadership, while translating complex program strategy into clear execution plans and measurable results.

This is a TPM-forward role, deep in Jira, comfortable with technical nuance, and fluent in aligning teams around what actually moves the bottom line.

The base compensation for this role is expected to range from $ 160,000 to $ 190,000per year. Actual compensation will be based on a variety of factors, including skills, experience, qualifications, and overall fit for the role.

Total compensation may include base salary, performance-based bonuses, equity, and benefits. Final offers are tailored to each candidate and take into consideration their background and years of experience.

This role follows a hybrid work model with a requirement of a minimum of three (3) days per week onsite. Employees should expect to work regularly from the office to support collaboration and business needs.

Key Responsibilities

Program Leadership & Execution

• Own and drive end-to-end technical programs across engineering and go-to-market teams, from strategy through execution and delivery.
• Serve as the single-threaded owner for complex, cross-functional initiatives with multiple stakeholders and dependencies.
• Break down ambiguous, complex program strategies into clear, executable roadmaps with defined milestones, risks, and success metrics.
• Ensure programs are delivered on time, on scope, and aligned to revenue and business impact.
  

Strategic Alignment

• Partner closely with the GM and senior leadership to ensure program priorities align with company vision, quarterly OKRs, and key business results.
• Continuously assess and adjust program scope based on bottom-line impact, customer value, and operational efficiency.
• Help teams define what matters most, prioritizing work that drives revenue, margin, scalability, and speed to market.
  

Cross-Functional Collaboration

• Act as the connective tissue between Engineering, Product, Marketing, Operations, and Business teams.
• Translate technical constraints and development nuances into language leadership can act on.
• Drive clarity and accountability across teams with different incentives, timelines, and perspectives.
  

Technical Program Management Excellence

• Be a Jira power user / guru owning workflows, dashboards, dependency tracking, and reporting.
• Implement and continuously improve program management processes, tooling, and operating rhythms that scale with the business.
• Proactively identify risks, blockers, and misalignment early and drive resolution.
  

Communication & Executive Readouts

• Deliver clear, concise, and compelling program updates to leadership, including progress, risks, tradeoffs, and recommendations.
• Synthesize complex technical and operational information into executive-ready narratives.
• Create transparency and trust through consistent, high-quality communication.

Requirements

Basic Qualifications

• Bachelors Degree Required
• 8+ years of experience in Technical Program Management, Program Management, or similar roles in fast-paced environments.
• Proven experience leading large, cross-functional technical programs with measurable business impact.
• Deep hands-on experience with Jira (advanced workflows, reporting, dependency management).
• Strong understanding of software development lifecycles, agile methodologies, and technical tradeoffs.
• Demonstrated ability to align execution with business outcomes, especially revenue-driven initiatives.
• Exceptional communication skills, able to influence engineers, marketers, and executives alike.
• Track record of thriving in startup or high-growth environments where ambiguity is the norm.

Preferred Qualifications

• Experience in e-commerce, marketplace, or apparel/retail technology.
• Background working closely with engineering teams (former engineer, technical degree, or equivalent exper