Motivate Venture Capital

About iink

iink is transforming how insurance claim payments are managed and disbursed across the property restoration ecosystem. Our platform serves Public Adjusters, Property Attorneys, Restoration Contractors, and the homeowners they work with. Additionally, we are expanding platform usage to enterprise mortgage servicers.

The iink platform is modernizing payment workflows and helping accelerate the recovery process for homeowners and stakeholders alike.

We are a growing technology company with ambitious goals, a strong product-market fit in our core verticals, and significant opportunity ahead.

Position Overview

iink is seeking a highly motivated, entrepreneurial Head of Sales to lead and expand our sales function. This is a hands-on player-coach role for someone who can set strategy, manage a team, and independently contribute by leading demos, developing pipeline, closing deals, and getting directly involved in the day-to-day work required to grow revenue.

The right candidate will have experience building and managing a go-to-market motion across both SMB and Enterprise customer segments. They should be comfortable driving a product-led sales strategy for SMB growth while also supporting larger, more complex enterprise opportunities.

This individual should thrive in ambiguity, move quickly in a venture-backed startup environment, and bring the operational discipline needed to help scale an early-stage sales organization. Experience in verticalized software, payments, or complex regulated industries such as financial services, healthcare, insurance, or mortgage servicing is strongly preferred.

As a member of the iink Leadership Team, this individual will work closely with company leadership to drive growth, improve sales processes, and help scale the business.

Key Responsibilities

Sales Leadership & Execution:

• Lead product demos and actively participate in the sales process
• Own and close key sales opportunities
• Develop and manage a healthy sales pipeline and funnel
• Build strong relationships with prospects and customers
• Drive revenue growth across both SMB and Enterprise customer segments
• Establish repeatable sales motions that support product-led SMB growth and complex enterprise sales

Team Leadership:

• Manage, coach, and develop a small team of SDRs
• Set clear sales accountability, metrics, and performance expectations
• Act as a hands-on player-coach, balancing team leadership with direct selling and execution
• Help recruit and scale future sales team members as the organization grows

Strategy & Growth:

• Help shape and execute iink’s go-to-market strategy across SMB, mid-market, and Enterprise segments
• Partner with leadership, product, customer success, and operations to improve conversion, activation, expansion, and sales execution
• Support expansion into new verticals and enterprise opportunities, including the mortgage servicer / Loss Draft segment
• Operate effectively in a fast-moving, ambiguous startup environment where priorities, processes, and systems continue to evolve

Ideal Candidate Profile

We recognize there are multiple backgrounds that could lead to success in this role. Strong candidates may include experienced B2B sales leaders, industry professionals with deep knowledge of iink’s markets, power users or existing customers of iink, or individuals who have helped scale growth-stage technology companies.

The ideal candidate combines:

• Strong sales leadership capability with a willingness to personally sell, execute, and get hands-on in the sales process
• Experience building and managing go-to-market motions across both SMB and Enterprise customer segments
• Demonstrated success developing repeatable sales processes, funnels, and pipeline discipline
• Experience defining or executing product-led sales or product-led growth strategies, particularly for SMB customers
• Comfort operating in a fast-moving, ambiguous, venture-backed startup environment
• Prior experience in verticalized software, payments, fintech, insurtech, healthcare technology, or other complex / regulated industries
• Familiarity with CRM systems, sales technology, and sales process optimization
• Excellent communication, presentation, relationship-building, and cross-functional collaboration skills
• Entrepreneurial drive, operational rigor, and a bias toward action

Growth Opportunity

This role is designed to grow alongside the company. As iink scales, the leadership scope may expand to include:

• Larger sales teams
• Additional SDRs and Account Executives
• Enterprise sales leadership
• Broader revenue operations responsibilities
• Expanded ownership of strategic market development

Compensation

iink offers a competitive compensation package including:

• Base salary of $85,000–$125,000 (depending on experience, skills, and location)
• Sales incentive compensation plan
• Equity participation
• Medical, dental, and vision insurance
• 401(k)
• Unlimited PTO

Why iink?

This is an opportunity to join a growing technology company at an exciting stage and play a major role in shaping its future. We are looking for someone eager to make an impact, build something meaningful, and grow with the business over the long term.

This is not a role for a purely strategic coach. We are looking for a player-coach who is excited to build, sell, lead, test, iterate, and get their hands dirty while helping shape the next stage of iink’s growth.

Interested?

Please email your résumé and cover letter to careers@iink.com with Head of Sales Opening as the subject line.