Artificial Intelligence (AI), Business-to-Business (B2B), Channel Sales, Coaching, Continuous Improvement, Cross-Functional, Customer Relationship Management (CRM), Dental Insurance, Exceeded Sales Goal, Field Sales, Finance, Forecasting, Inside Sales, Leadership, Legal, Merchant Services, Metrics, Non-Profit Funding, Operations, Operations Processes, Prescription Drugs, Process Modeling, Product Marketing, Productivity Management, Revenue Planning, Revenue/Sales Reporting, Sales, Salesforce.com, Solution Sales, Team Lead/Manager, Tuition Reimbursement, Vision Plan
Description
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.
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.
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.:
- Own and deliver against the company’s Q3 & Q4 2026 Corporate Reward revenue targets, which will be defined and communicated upon hire.
- Achieve the Q3 and Q4 Merchant Solutions new business revenue goal
- Grow our primary product (PerfectGift+) to reach 8%+ of total monthly sales
- With the launch of our new CareTap product in Q3, sign up 25+ new corporate accounts by the end of 2026.
- During H2, engage F2F with a minimum of 10 new prospects/clients in support of Corporate Reward revenue attainment and 5 merchant prospects in support of Merchant Solutions goals.
Qualifications
- 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.
- Experience in B2B or FinTech industries is preferred; familiarity with payments or merchant solutions is a plus.
- 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.
Compensation, Benefits, and Perks
The compensation shown includes Base Salary plus Target Incentives Bonus. In addition, you will receive RSUs. 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)
- 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