Head of Sales - Fintech SMB Growth & Scale

Affiniti; New York (NY); On-site; USD 180,000 - 270,000; Full time

Benefits offered by this job

Relocation reimbursement

Free lunch and dinner (in person)

Paid technology equipment setup

Health, Dental, and Vision insurance

Job summary

Affiniti, a fintech company transforming spend management for small businesses, is hiring a Head of Sales to design and scale its next GTM phase. Based in NYC (on-site), this leadership role blends hands-on execution with building systems, managers, and culture to drive a high-velocity SMB sales organization.

The ideal candidate brings 6–15 years in senior sales roles, a track record of beating quotas, and the ability to hire and coach SDRs and AEs.

Qualifications

• 6-15 years of sales experience, including meaningful experience managing and scaling high-velocity sales teams.
• Current or recent VP-level, Director-level, or Head of Sales experience in fintech, payments, banking, expense management, SMB SaaS, or adjacent financial software.
• Proven success selling into SMB or lower mid-market customers, with less than $50M in revenue.
• Track record of beating departmental quotas, not just hitting them.
• Strong understanding of SMB buyer behavior and decision factors.
• Experience managing SDR and AE teams with improved pipeline generation and quota attainment.
• Strong outbound sales motion experience: targeting, sequencing, qualification, discovery, and coaching.
• Ability to build practical sales infrastructure without over-engineering the motion (CRM hygiene, dashboards, forecast cadence).
• Strong coaching orientation to develop early-career sellers and raise performance.
• Experience hiring and assessing sales talent, distinguishing between title and scope.
• Hands-on builder mindset with analytical and operational instincts.
• Clear, direct communicator who can align with cross-functional partners.

Responsibilities

• Own the SMB and lower mid-market sales strategy including segmentation, account targeting, and revenue planning.
• Drive consistent new business performance across the full sales cycle from outbound to close.
• Build and refine a repeatable high-velocity sales motion for SMB buyers.
• Lead, coach, and develop SDRs and AEs for strong execution and pipeline creation.
• Establish outbound standards, pipeline coverage, and conversion metrics.
• Create practical sales playbooks for prospecting, discovery, objections, positioning, and close plans.
• Own forecasting, pipeline inspection, performance reporting, and revenue metrics for founders.
• Partner with Marketing, Product, Customer Success, and Operations to improve messaging and efficiency.
• Define a high-intensity, high-accountability sales culture with strong coaching and talent development.

Skills

Sales leadership

Go-to-market strategy

Forecasting & analytics

Team coaching

Outbound sales

Cross-functional partnership

Recruiting & hiring

Job description

Affiniti, a fintech company transforming spend management for small businesses, is hiring a Head of Sales to design and scale its next GTM phase. Based in NYC (on-site), this leadership role blends hands-on execution with building systems, managers, and culture to drive a high-velocity SMB sales organization.

The ideal candidate brings 6–15 years in senior sales roles, a track record of beating quotas, and the ability to hire and coach SDRs and AEs.