Senior Outside Sales Executive

PerfectGift.com is seeking a high-performing Senior Outside Sales Executive with demonstrated experience in the prepaid, stored value, loyalty, rewards, and incentive ecosystem, as well as API-driven platforms and integrations. This role is responsible for driving new revenue through vertically focused sales efforts while representing a comprehensive portfolio of prepaid Visa/Mastercard, digital choice products, and incentive solutions across multiple industries. The ideal candidate understands the nuances of the stored value and prepaid payments industry, including program structure, funding models, compliance considerations, and partner ecosystems, and is comfortable engaging in conversations involving platform capabilities, API integrations, and technical onboarding workflows. This individual thrives in consultative selling environments, builds strong long-term relationships, and consistently exceeds revenue targets. Responsibilities Generate net-new API and enterprise opportunities across target verticals (HR/Benefits, Financial Services, Gaming/Hospitality, Healthcare, Retail, Technology/SaaS) through cold outreach, referrals, and industry events. Run the full sales cycle end to end, including discovery, platform demos, pricing, negotiation, and close, and lead the most complex, multi-stakeholder API-integration pursuits with technical discovery, sandbox coordination, and onboarding workflows. Maintain a 3x+ pipeline through consistent outbound prospecting, disciplined follow-up, and accurate deal-stage tracking in HubSpot. Expand existing accounts through upsell and program expansion, and partner with Product, Compliance, and Client Success to move clients from signed to launched. Represent PerfectGift.com at trade shows, conferences, and partner meetings, traveling approximately 35–40% to support client meetings and field prospecting. 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: Complete onboarding across product, verticals, and the core sales stack (HubSpot, ZoomInfo, Aircall, GovSpend, LinkedIn Sales Navigator), and add 250+ qualified leads to CRM by day 30. Build an active pipeline of 10+ viable opportunities and set 5+ qualified meetings per week by day 60, sustaining 200+ outbound touches weekly. Close 2+ deals by day 90 while maintaining 300+ outbound touches per week and attending 3+ networking or industry events. Qualifications 10+ years of outside/outbound B2B sales experience in prepaid, stored value, payments, loyalty, rewards, incentives, or adjacent FinTech industries, with a sustained track record of carrying and beating a large quota. Demonstrated success leading and closing complex enterprise or mid-market deals across verticals such as HR/Benefits, Financial Services, Healthcare, Retail, Gaming/Hospitality, or Technology/SaaS. Deep, hands-on experience selling API-based or SaaS platforms, including the ability to lead technical discovery across API documentation, sandbox testing, webhooks, and integration onboarding. HubSpot CRM proficiency with a disciplined approach to pipeline forecasting, deal stages, and data hygiene under full quota accountability. Operates with high autonomy and serves as a trusted expert and informal resource for other sellers, builds durable long-term client relationships, and is willing to travel 35–40%. 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