Head of Sales

Fintech has existed for decades. Yet walk into almost any pharmacy, vet clinic, or local HVACR shop in America and you'll find the same story: a business owner managing their finances with tools that haven't meaningfully evolved since their parents ran the place. That gap is what Affiniti is closing.

Affiniti is entering its next stage of GTM growth. The team has validated early sales motion, improved the rep profile, and is now preparing to scale a high-velocity sales organization.

Affiniti is hiring a Head of Sales to build and lead the company’s next chapter of go-to-market scale. This leader will inherit an early sales motion, sharpen the playbook, raise the talent bar, and scale a high-velocity SMB sales organization.

This is a hands-on leadership role for a sales leader with experience in a fast-paced fintech, payments, spend management, or SMB software environment. The right person will bring the operating intensity to manage today’s team closely while building the systems, managers, and culture required for a much larger organization.

This is an opportunity to build and scale the sales function at a high-growth fintech company, with direct partnership with the founders and leadership team and meaningful ownership over sales strategy, team design, hiring, and GTM execution.

About Affiniti, and who we look for:

LOCATION

NYC (On-Site)

EXPERIENCE

6-15 YOE including meaningful experience managing and scaling high-velocity sales teams.

TOTAL COMPENSATION

Competitive cash compensation aligned to experience and stage

Equity package commensurate with seniority and impact

BENEFITS

Reimbursed Relocation

Free Lunch and Dinner (In Person Only)

Paid Technology Equipment Set Up

Health, Dental, and Vision Insurance Fully Paid

Key Responsibilities

Sales Strategy: Own the sales strategy for SMB and lower mid-market customers, including segmentation, customer prioritization, sales motion design, and revenue planning.

Revenue Execution: Drive consistent new business performance across the full sales cycle, including outbound prospecting, qualification, discovery, demos, proposal management, negotiation, and close. We take department-level quota seriously, and expect you to consistently exceed it, not simply meet it.

High-Velocity Sales Motion: Build and refine a repeatable sales process suited for SMB buyers, shorter sales cycles, efficient rep productivity, and clear conversion metrics across the funnel.

Team Management: Lead, coach, and develop SDRs and AEs, ensuring strong execution across activity quality, messaging, discovery, pipeline creation, follow-up, and closing discipline.

Pipeline Generation: Establish the standards, systems, and operating cadence for outbound sales, account targeting, lead qualification, pipeline coverage, and conversion from first touch to closed-won.

Sales Playbooks: Create practical sales playbooks for prospecting, discovery, objection handling, competitive positioning, buyer education, close plans, and handoffs.

Forecasting and Reporting: Own forecasting, pipeline inspection, performance reporting, and sales metrics, giving the founders clear visibility into what is working, what is not, and where to intervene.

Hiring and Team Design: Partner with the founders to hire and develop a mix of proven SMB fintech sellers and high-potential startup operators who can thrive in a fast-moving environment.

Performance Management: Set clear expectations for rep performance, establish operating rhythms, and create accountability around inputs, outputs, and revenue outcomes.

Cross-Functional Partnership: Work closely with Marketing, Product, Customer Success, and Operations to improve messaging, lead flow, onboarding, customer experience, and revenue efficiency.

Culture Building: Help define the standards for a high-intensity, high-accountability sales culture while maintaining strong judgment around coaching, talent density, and long-term team development.

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, ideally within fintech, payments, banking, expense management, bill pay, SMB SaaS, or adjacent financial software.

Demonstrated success selling into SMB or lower mid-market customers, particularly businesses with less than $50M in revenue.

Have a clear track record of beating departmental quotas, not just hitting them.

Strong understanding of SMB buyer behavior, including how small business owners and operators evaluate financial products, software, ROI, trust, urgency, and ease of implementation.

Experience managing both SDR and AE teams, with a track record of improving pipeline generation, conversion rates, quota attainment, and rep productivity.

Strong command of outbound sales motions, including account targeting, sequencing, messaging, qualification, discovery, and sales manager inspection.

Ability to build practical sales infrastructure without over-engineering the motion, including CRM hygiene, dashboards, pipeline stages, qualification criteria, forecasting cadence, and performance reporting.

Strong coaching orientation, with the ability to develop early-career sellers, improve rep fundamentals, and raise the overall bar for sales execution.

Experience hiring and assessing sales talent, including the ability to distinguish between title, true scope, sales motion fit, team size managed, and actual operating impact.

Ability to operate as a hands-on builder rather than a purely strategic executive.

Strong analytical and operational instincts, with the ability to diagnose funnel performance and translate insights into action.

Clear, direct communicator who can set expectations, hold teams accountable, and build trust across functions.

Cross-functional understanding of adjacent business functions, including how customer operations and success tie into sales, how marketing and sales work together to maximize output, and more.

What Will make Someone Successful

Intensity without chaos: Brings urgency, accountability, and pace while creating clarity for the team.

Builder mindset: Wants to design the system, not just inherit one.

Pragmatic process: Knows which operating mechanisms matter at this stage and avoids overbuilding the sales process too early.

Strong coaching muscle: Improves rep performance through specific feedback, clear expectations, and consistent inspection.

Customer empathy: Can connect with traditional SMB operators and translate their needs into a sales motion that feels practical, credible, and useful.

High standards for talent: Raise the bar on hiring and performance while retaining the scrappiness that early-stage teams require.

Do what it takes: whether that means taking demos to bridge a revenue gap, getting involved in outbounding, or jumping into whatever else is needed, no job is beneath you.

Intense Perfection Barometer: be the type of person who catches what everyone else overlooks. If there’s a misspelling in an email, grill the SDR. If someone shows up with low energy, call it out. Operate with precision, and an intolerance for sloppy execution. Push the standard until carefulness becomes the b