Head of Sales

Flourish Ventures; United States; On-site; USD 175,000 - 225,000; Full time

Job summary

TrueBiz is a YC-backed merchant risk intelligence platform helping financial institutions understand whether the businesses they serve are legitimate. We are a lean, founder-led team that rewards ownership and impact, seeking a Head of Sales to personally win our next generation of strategic customers and eventually build a small, exceptional sales team around what works.

You will lead and close strategic enterprise opportunities, build relationships with senior leaders across risk, fraud,

Qualifications

• Has consistently been a top enterprise seller.
• Has personally closed complex six- and seven-figure B2B deals.
• Knows how to navigate large organizations with multiple stakeholders.
• Wants to remain close to customers and deals rather than becoming a full-time manager.
• Experience selling into payments, fintech, fraud, risk, identity, compliance, financial services, or enterprise data is valuable.

Responsibilities

• Personally lead and close strategic enterprise opportunities.
• Build relationships with senior risk, fraud, underwriting, compliance, and product leaders.
• Own a meaningful individual pipeline and revenue target.
• Work directly with the CEO on our largest and most strategic accounts.
• Navigate complex sales processes involving product, technical, procurement, security, legal, and executive stakeholders.
• Take the sales motion we've already developed and make it significantly better.
• Identify what separates deals that move quickly from those that stall.
• Sharpen qualification, discovery, messaging, account strategy, and deal execution.
• Develop repeatable approaches for breaking into and expanding within large financial institutions.
• Establish a simple and accurate forecasting and pipeline-management cadence.
• Turn founder-led knowledge into a sales process that other strong sellers can execute.
• Coach and develop a lean sales team.
• Determine when additional sales capacity is actually needed.
• Recruit a small number of exceptional sellers rather than building ahead of demand.
• Establish expectations, compensation, territories, and operating cadence.
• Stay directly involved in selling even as the team grows.

Skills

Enterprise selling

Complex deals

Pipeline forecasting

Stakeholder navigation

Team-building

Job description

TrueBiz

Instant Background Checks for Businesses

Head of Sales

$175K - $225K US / CA / Remote (US; CA)

• Job type Full-time
• Role Sales
• Experience 6+ years
• Visa US citizen/visa only

Connect directly with founders of the best YC-funded startups.

Danny Hakimian

Founder

Danny Hakimian

Founder

About the role

TrueBiz is a YC-backed merchant risk intelligence platform helping financial institutions understand whether the businesses they serve are legitimate.

We're at a rare stage as a company: we already work with some of the largest companies in payments and financial services, but we're still a small team where exceptional people can have an enormous impact on what gets built and how the company develops.

We've intentionally stayed lean, moved quickly, and given people much more ownership than they would typically have at a company with our level of enterprise traction. There are very few layers between identifying an important problem and actually solving it.

The mission matters too. Our technology helps stop fraudulent and abusive businesses from gaining access to the financial system, while helping legitimate businesses get approved faster and with less friction.

We've gotten this far with a predominantly founder-led sales motion and the beginnings of a repeatable playbook. We're now looking for a Head of Sales to build on that foundation, personally win our next generation of strategic customers, and eventually build a small, exceptional sales team around what works.

What you'll own

Sell

• Personally lead and close strategic enterprise opportunities.
• Build relationships with senior risk, fraud, underwriting, compliance, and product leaders.
• Own a meaningful individual pipeline and revenue target.
• Work directly with the CEO on our largest and most strategic accounts.
• Navigate complex sales processes involving product, technical, procurement, security, legal, and executive stakeholders.

Build the playbook

• Take the sales motion we've already developed and make it significantly better.
• Identify what separates deals that move quickly from those that stall.
• Sharpen qualification, discovery, messaging, account strategy, and deal execution.
• Develop repeatable approaches for breaking into and expanding within large financial institutions.
• Establish a simple and accurate forecasting and pipeline-management cadence.
• Turn founder-led knowledge into a sales process that other strong sellers can execute.

Build the team

• Coach and develop a lean sales team.
• Determine when additional sales capacity is actually needed.
• Recruit a small number of exceptional sellers rather than building ahead of demand.
• Establish expectations, compensation, territories, and operating cadence.
• Stay directly involved in selling even as the team grows.

We expect the sales organization to remain lean by design.

What we're looking for

We're less interested in a specific title than evidence that you can both sell and build.

You are likely someone who:

• Has consistently been a top enterprise seller.
• Has personally closed complex six- and seven-figure B2B deals.
• Has experience creating pipeline rather than relying entirely on inbound demand.
• Knows how to navigate large organizations with multiple stakeholders and long sales cycles.
• Is comfortable hiring slowly and maintaining a high talent bar.
• Is rigorous about pipeline and forecasting without introducing unnecessary bureaucracy.
• Wants to remain close to customers and deals rather than becoming a full-time manager.

Experience selling into payments, fintech, fraud, risk, identity, compliance, financial services, or enterprise data is particularly valuable.

What success looks like

First 30 days

• Develop a deep understanding of TrueBiz, our customers, existing pipeline, and current sales playbook.
• Join active opportunities and begin taking ownership of deal strategy.
• Build account plans for our highest-priority prospects.
• Understand what has driven our largest wins so far and where our current process breaks down.
• Develop a strong working cadence with the CEO and existing AE.

First 90 days

• Personally own and advance a meaningful pipeline of strategic opportunities.
• Improve our sales playbook based on firsthand experience selling the product.
• Put in place a simple, reliable qualification and forecasting process.
• Establish a repeatable approach to penetrating our highest-value target accounts.
• Coach the existing AE and create clear standards for how we sell.
• Define what the next 1–2 sales hires should look like and when we should make them.

Over the following 12 months

• Become a major individual contributor to new revenue.
• Build a small team of exceptional enterprise sellers around you.
• Create a sales motion that generates predictable pipeline and closes large accounts without depending entirely on the CEO.
• Maintain a high revenue-per-salesperson culture as the company grows.

How we work

TrueBiz is an intentionally lean and experienced team.

You'll have direct access to the CEO, product, and engineering team. Decisions happen quickly, and there are very few layers.

That also means there won't be a large organization around you to solve problems. We expect you to identify what needs to happen and make it happen.

For the right person, that's the opportunity: take a sales motion that has already produced major enterprise customers, improve it through your own selling, and build the small team that can take it much further.

About TrueBiz

We're revolutionizing risk management and business onboarding for financial services. Our solution automates the analysis of a business' web presence and internet reputation in under 30 seconds using LLMs, dramatically speeding up the underwriting process.

Our technologies have been successfully implemented by industry leaders such as Visa, Lightspeed, top US acquiring banks and global fintechs. We've raised $2.4M from Y Combinator, Flourish Ventures, Homebrew, Fintech Fund, and prominent fintech angels.