Executive Director - Ascender (Pittsburgh)

Work In Progress Consulting•East Liberty, PA

23h•Hybrid

About The Position

Ascender is Pittsburgh’s cross-sector entrepreneur community, operating as a coworking space, founder hub, and programming organization serving 300 community members annually. It uniquely brings together tech founders, Main Street business owners, and service entrepreneurs. Ascender offers resources such as coworking space, business mentorship, educational programming, and access to experts. The organization's core belief is that peer relationships foster opportunity, leading to introductions, problem-solving, and trust-building within its community. Ascender is distinguished by its inclusive approach, prioritizing cross-sector and cross-class connections to drive individual success and regional economic mobility, with its Bootcamp and Incubation programs supporting historically excluded founders. The organization is at a pivotal moment of evolution, with a strategic commitment to shifting its financial model towards earned revenue from membership, programming, and partnerships, while continuing to value foundation support. The goal is to reach 175-200 members and significantly increase earned revenue by the end of 2027. The next Executive Director will spearhead this transition, requiring expertise in organizational and business strategy, fundraising, external relations, and partnership development. This role demands a leader who can articulate Ascender's value proposition, inspire investment, and execute the vision, all while upholding Ascender's core values: Keep it Real, Keep it Human; Raise the Bar, Every Day; Own the Outcome; One Team, One Mission; and Protect Our Reputation.

Requirements

7-10 years of progressive leadership experience in nonprofit organizations, fundraising, entrepreneurship support, small business development, or a related field.
Demonstrated ability to cultivate and steward philanthropic, corporate, and other funder relationships; Experience making direct asks and securing 6-and-7-figure gifts.
Experience in developing and adjusting business models
Ability to effectively manage and steward an annual budget of up to $1.5M+ while increasing and diversifying revenue streams.
Experience leading organizational change or transitions (model shifts, leadership transitions, space moves).
Excellent communication, storytelling, and listening skills, with the ability to articulate vision and serve as Ascender’s primary spokesperson.

Nice To Haves

Understanding of Pittsburgh’s philanthropic, civic, or entrepreneurship ecosystem and/or ability to learn and navigate those relationships quickly.
An understanding of systemic inequities in the entrepreneurial sector with a track record of designing or supporting initiatives that expand access and reduce barriers.
A healthy and inclusive leadership approach.
Ability to work effectively as part of a leadership team, prioritizing transparency, shared responsibility, and collective problem-solving.
Ability to hold and prioritize multiple tasks in a fast moving environment.
Personal familiarity with entrepreneurship or business ownership is a plus.

Responsibilities

Ideates and drives progress on the organization’s strategic path to revenue growth through funder relationships, business development, earned revenue, and sponsorship without losing sight of the organization’s mission.
Leads cultivation, stewardship, and solicitation of foundation grants, corporate sponsorships, and individual donors. Maintains and grows existing relationships with key institutional funders.
Aligns programming and membership, coworking operations, partnerships, revenue strategy, and resource allocation into a unified growth model with measurable objectives.
Ensures strategy and operations are in line with organizational financial health benchmarks including operating reserves, earned revenue growth, and revenue growth.
Leads adaptive strategy and execution by proactively identifying organizational risks and strategic openings, using data to inform decisions, and adjusting priorities, plans, and operations in real time.
Makes final decisions on strategic investments, new initiatives, and organizational tradeoffs.
Serves as Ascender’s primary external spokesperson. Owns Ascender’s theory of change, articulates vision, and positions the organization within Pittsburgh’s entrepreneurship, civic, and philanthropic ecosystems.
Identifies, cultivates, and sustains strategic partnerships and relationships. Partners with the staff and Board to steward funder relationships, develop corporate engagement strategies, and identify and manage strategic partnerships.
Acts as the primary liaison with Ascender’s Board of Directors. Ensures board members are informed, engaged, and activated. Supports board committees and special initiatives.
Works with the team to prepare and present reporting for the Board of Directors, funders, sponsors, donors and other relevant stakeholders.
Ensures the organization sustains an inclusive, welcoming environment for all partners, members, and team members. Actively develops practices that are relevant, useful, and responsive for bridging differences across identities and business types.
Holds overall responsibility for outputs of the entire Ascender team, including managing three direct reports: Executive Assistant, Operations Director and Programs Director.
Cultivates an inclusive, supportive team environment where individuals can show up authentically, are encouraged in their professional growth, and are supported in maintaining healthy work–life boundaries.
Supports consistent accountability and performance management standards that support follow-through, transparency, and entrepreneurial thinking.
Models healthy delegation by clearly defining desired outcomes, empowering team members with autonomy and trust to determine how work gets done.
Works in partnership with the Operations Director, Board and accounting team to enact strong fiscal management of Ascender. Responsible for ensuring legal and financial compliance.
Works in partnership with the Programming Director to develop and/or oversee systems for identifying, tracking, monitoring, and reporting on key metrics, grant deliverables, progress towards goals, and effectiveness of strategies. Regularly assesses whether services and operations are aligned with stated values and strategic intent.
Leads and/or oversees major facility decisions and the coworking space as a strategic asset. Partners with the Board’s ad hoc space committee, including facilitating a possible lease renegotiation and/or relocation in 2028.

Benefits

Flexible hybrid work schedule including Ascender Fridays, with option to leave at 2pm.
Option to work up to 3 days remotely per week.
100% medical, dental, and vision benefits via UPMC Health Plan
10 vacation days, 5 sick days for the first year
11 holidays
Paid weeklong office closures in August and December
Annual professional development stipend
Monthly cell-phone reimbursement
Paid parental and medical leave
401k with employer match after the first year of employment