Enterprise Sales Lead

About Howard Financial

Howard Financial is a full-service back-office solution for companies and entities with bookkeeping, payroll, and bespoke reporting needs that require accuracy, timeliness, and institutional-quality reporting without the burden of full-time staff.

We are an experienced team of bookkeepers and administrators with multiple decades of combined experience across industries allowing companies to focus on their core business while we handle the rest.

Founded in 2023, our team of 60 professionals supports ~40 clients across a diverse range of industries. We recently reached $5M of contracted ARR and are growing rapidly (over 150% MRR growth YTD).

About the role

We are now looking for a hungry and entrepreneurial Enterprise Sales Lead to drive new business with growth-stage companies and funds. This is a critical early hire that will help define Howard’s go-to-market motion while working closely with leadership, client teams, and operations.

What you'll do

Drive new business through outbound sales, inbound qualification, and relationship building

Close high-value deals with startups, funds, and high-net-worth operators

Collaborate closely with Company leadership on sales strategy, pricing, and growth experiments

Design and maintain accurate pipeline tracking

Lead initial onboarding alongside the client delivery team to ensure smooth handoff and client success

Represent Howard at industry events, conferences, and strategic meetings

Provide feedback to product, marketing, and operations to continually improve our offering

Over time, lead effort to build out a scalable sales organization as Howard continues to grow

Qualifications

Driven, competitive, and highly motivated by upside compensation

Comfortable working in a fast-paced, ambiguous startup environment

5+ years of experience in B2B sales, ideally in financial services, SaaS, or consulting

Proven ability to close 6-figure deals and hit aggressive quotas

Excellent written and verbal communication skills

Strong understanding of financial services or comfort selling to CFOs and fund managers

Experience with CRMs and modern sales tools

Values culture, ownership, and teamwork

Compensation & Benefits

Competitive compensation package: Annual base salary with a on-target earnings (OTE) structure. The variable component is tied to clear, performance-based targets, with incentive bonuses paid quarterly.

High upside potential: This role is designed for someone motivated by meaningful variable compensation and long-term earning potential as we scale.

Early-team ownership: Opportunity to shape our sales strategy, processes, and culture as a key early hire.

Growth and leadership track: As we expand, this role will evolve into building and leading a scalable sales organization.

Benefits: Flexible work environment, and the autonomy and responsibility that come with joining a fast-moving, entrepreneurial team.