VP of Sales
About The Position
We are looking for a results-driven VP of Sales to lead and scale our revenue organization at a pivotal moment in our company’s growth. As we continue to embed AI across our products, processes, and daily operations, you will join a company that is actively transforming the way financial technology is built and sold — and you will be expected to bring that same forward-thinking mindset to the sales organization. Reporting to senior leadership, this role owns the full commercial engine: Outside Sales, Inside Sales, and the outbound sales for Merchant Solutions, with a team of roughly 20 sales professionals. If you thrive in fast-moving environments, have a strong command of B2B and FinTech sales motions, and are energized by building revenue-generating machines, this is the opportunity for you. This is a 5-day onsite role in Pittsburgh, PA, with regular travel for client & prospect visits expected.
Requirements
- 8+ years of progressive sales leadership experience, with at least 3 years managing multi-team or multi-channel sales organizations.
- Demonstrated track record of hitting or exceeding revenue targets in a B2B or SMB sales environment.
- Proven ability to recruit, develop, and retain high-performing sales talent in a fast-paced, execution-focused organization.
- Highly data-driven with strong CRM proficiency (e.g., Salesforce or equivalent) and the ability to build and maintain reliable forecasting processes.
- Comfortable operating in an AI-forward work environment and actively leveraging technology to improve team productivity and sales outcomes.
Nice To Haves
- Experience in B2B or FinTech industries is preferred; familiarity with payments or merchant solutions is a plus.
Responsibilities
- Own and drive overall revenue performance across Outside Sales, Inside Sales, as well as the outbound sales for Merchant Solutions, holding the organization accountable to quarterly and annual targets.
- Lead, coach, and develop the sales team, setting clear performance expectations and building a culture of accountability and continuous improvement.
- Unify the Corporate Reward and Merchant Services sales organizations under a single operating model, standardizing processes, tools, and reporting while preserving the product expertise that makes each team effective in its market.
- Improve upon and enforce our sales processes, CRM hygiene, and forecasting cadences to deliver predictable, data-driven revenue reporting to leadership.
- Collaborate cross-functionally with Product, Marketing, Finance, Legal, and Operations to align on customer needs, refine the value proposition, and accelerate the adoption of AI-enabled tools within the sales workflow.
Benefits
- Restricted Stock Units (RSUs)
- Incentive Bonus
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
