Program Manager to the CEO

Wolfe, LLC; Pittsburgh (Allegheny County); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Restricted Stock Units (RSUs)

Profit Share

Medical, Prescription, Vision, and DnD

Short-Term Disability Insurance

Long-Term Disability Insurance

PTO

401(k)

Tuition Reimbursement

Team outings

Job summary

Wolfe, LLC in Pittsburgh, PA, seeks a hands-on Project Manager to be the CEO's right hand for technology and data initiatives. This 5‑day onsite role requires coordinating with product and engineering, and driving multiple workstreams to successful delivery.

You will produce executive-ready deliverables, manage operations and vendor projects, and leverage AI‑assisted tools to triage requests and maintain a real‑time view of work in flight.

Qualifications

• 7+ years of combined tech work and project/operations delivery.
• Technically capable to own AI and systems projects with product/engineering.
• Proven ability to manage many concurrent workstreams to completion.
• Comfortable switching between high-value tech work and operational tasks.
• Proficient with PM tools (Monday.com/Jira) and AI-assisted tooling.

Responsibilities

• Keep multiple concurrent workstreams organized and tracked to completion.
• Own technical and AI projects from scoping to delivery with product/engineering.
• Produce and clean up CEO-facing deliverables: reports, presentations, follow-ups.
• Coordinate operational and property matters end to end with vendors and teams.
• Use AI-assisted tools to triage requests and surface CEO items.

Skills

7+ years experience

Technical background

Multi-stream PM

PM tools proficient

AI tooling familiarity

Tools

Monday.com

Jira

AI tooling

Job description

Wolfe is a Pittsburgh-based FinTech company building the next generation of financial products, and we are actively embedding AI across our product, our internal processes, and the way our teams work day-to-day. As Project Manager to the CEO you will be the CEO's right hand for getting mostly technology related and data related projects done. You will also help with projects relating to properties we own, businesses we rent etc. Managing the projects and making sure they are being competed. A versatile technology minded project manager is ideal. This is a 5-day onsite role in Pittsburgh, PA.

Responsibilities:

• Keeping many concurrent, unrelated workstreams organized, tracked, and moving to completion using Monday.com, Jira and Ai.
• Own technical and AI projects directly, from scoping through delivery, partnering with product and engineering where needed.
• Produce and clean up the business deliverables the CEO relies on, including reports, presentations, and follow-up on open items.
• Coordinate operational and property matters end to end, managing the people and vendors involved through completion and CEO sign-off.
• Use AI-assisted tools to triage incoming requests, maintain a current view of all active items, and surface what needs the CEO's attention.

Impact Statement:

For more clarity on the role, below are the success metrics and measurements for this role in the first 90 to 120 days.:

• Take over a defined set of the CEO's current items within the first 30 days and establish a single tracked view of everything in flight, with a clear status on each.
• Stand up a repeatable intake and triage process for new items the CEO hands off, with a defined turnaround for acknowledgment and next steps.

Qualifications:

• 7+ years of combined professional experience spanning technical work (software development, product management, or similar) and running projects or operations, including hands-on delivery, not just oversight.
• Genuinely technical: able to own AI and systems projects directly and engage credibly with product and engineering, ideally from a software development or product management background.
• Proven track record managing many concurrent, unrelated workstreams to completion, with the organization and follow-through to keep nothing from slipping.
• Versatile and low-ego, comfortable moving between high-value technical work and hands-on operational or personal items as priorities demand.
• Hands-on with project and work-tracking tools (Monday.com or equivalent) and AI-assisted tooling; excellent communication, high ownership, and the discretion to work directly with a CEO on sensitive business and personal matters.

Compensation, Benefits, and Perks:

Wolfe is committed to providing a comprehensive benefits package to support your well-being, along with competitive compensation. Our benefits and perks include but not limited to:

• Restricted Stock Units (RSUs)
• Profit Share
• Medical, Prescription, Vision, and Dental insurance for employees and dependents (Wolfe pays 80% of premium)
• Short-Term Disability Insurance (Wolfe pays 100% of premium)
• Voluntary Long-Term Disability Insurance, Life Insurance, Critical Illness Insurance, Accident Insurance, and Hospital Indemnity coverage
• PTO (vacation and sick time)
• Corporate Holidays and Floating Holidays
• 401(k)
• Employee recognition program
• Charitable Donation to a charity of your choice yearly
• Employee Referral Bonus
• Tuition Reimbursement
• Internal Training and Information sessions
• Family Picnic, Holiday Party, and other outings
• Internal Culture Club

About Wolfe, LLC:

Wolfe, LLC is a pioneering force in e-commerce since 1996 and the gifting industry, deeply rooted in Pittsburgh, Pennsylvania. Driven by our vision "To move humanity to express love for each other through personalized, faster, beautiful, secure, flexible gift giving," we're on a mission to revolutionize the way gifts are given and received. We achieve this through high-quality, fast service, and the same-day delivery of customized gift cards from our on-demand nations only robotic fulfillment center, alongside offering a safe and flexible card-to-card gifting technology.

At the heart of our success are our Core Values: Teamwork, Drive, Integrity, Caring, and Excellence. These principles guide us as we innovate and expand our portfolio with platforms and brands like PerfectGift, Gift Card Granny, GiftYa, Reaf Marketing, and Give InKind, setting new standards in the gifting experience.

Some of the Company and Executive Team Recognitions:

2023 Inc. 5000 list of fastest-growing private companies (ranked no. 382)

2022 - 1st place - Fastest 50 Growing Companies in Pittsburgh, Pittsburgh Business Times

2020 The Best Places to Work, Pittsburgh Business Times

2017 - Winner of Outstanding Entrepreneur, Pittsburgh Venture Capital Association

2015 - Winner of Business Times Diamond Award, Business Ethics Award, Create Award

2015 CEO of the Year, Pittsburgh Technology Council