About Simply Bail

Simply Bail is modernizing one of the most overlooked industries in America.

Every day, bail bond agencies help families navigate some of the most stressful moments of their lives—but many still rely on outdated systems, paperwork, and manual processes. We've built a modern software platform that helps agencies run their businesses more efficiently while delivering a better experience for both agents and the people they serve.

Our platform brings everything together in one place—from case management and payment plans to e-signatures, court reminders, GPS check-ins, reporting, and automated communications—helping agencies close more business, reduce risk, and spend more time serving their customers.

We're an early-stage startup with big ambitions. We move quickly, solve real problems, and work directly with our customers to build software that makes a meaningful impact. If you're excited by ownership, autonomy, and the opportunity to help build something from the ground up, we'd love to meet you.

What You'll Do

Own Your Territory

Prospect, build relationships, and develop new business opportunities from the ground up.

Manage the Full Sales Cycle

Own deals from first conversation through close. You'll generate pipeline, qualify opportunities, overcome objections, and consistently close new business.

Become a Trusted Advisor

Learn your customers' businesses, understand their challenges, and help them adopt technology that makes them more efficient and more profitable.

Operate Like an Owner

We're looking for someone who doesn't wait for direction. You'll identify opportunities, test new ideas, and help shape how we sell.

Keep Momentum High

Follow up relentlessly, maintain an active pipeline, and consistently create opportunities through outbound prospecting and relationship building.

Stay Organized

Maintain accurate customer records, pipeline activity, and forecasting in our CRM.

Help Build the Company

As one of our early sales hires, your feedback won't just influence revenue—it will help shape our sales process, product roadmap, and go-to-market strategy.

Who We're Looking For

We're less interested in finding someone with the "perfect" résumé and far more interested in finding the right person.

The ideal candidate is someone who is naturally competitive, genuinely enjoys building relationships, and isn't afraid to roll up their sleeves. You're resourceful, coachable, and motivated by winning.

You likely have:

• 5–7 years of quota-carrying sales experience
• A track record of prospecting, building pipeline, and closing new business
• Experience selling into small businesses, owner-operators, or relationship-driven markets
• A self-starter mentality—you thrive with autonomy and don't need someone looking over your shoulder
• Strong emotional intelligence and the ability to connect with people from all walks of life
• High grit, resilience, and a strong work ethic
• A competitive personality and genuine hunger to succeed

Experience selling technology, SaaS, financial services, logistics, or operational software is helpful—but we care much more about personality, drive, and your ability to build trust than your industry background.

This is not the right fit for someone looking for a polished enterprise sales organization with layers of management and established playbooks.

It is the right fit for someone who enjoys figuring things out, loves talking to small business owners, and wants to help build a company from an early stage.

Why Join Simply Bail?

Build Something That Matters

Help modernize an industry that has been overlooked for decades while making life easier for the businesses serving their communities.

High Ownership

Your work will directly influence our growth, product direction, and sales strategy.

Startup Environment

Fast-moving, collaborative, and built for people who enjoy solving problems and creating opportunities.

Work Directly with Leadership

You'll partner closely with the founders and have real visibility into the business.

Compensation & Benefits

• Base salary: $90,000–$120,000
• $110,000-140,000 On-Target Earnings (OTE)
• Equity
• Healthcare benefits
• Significant opportunity for growth as the company scales