Director – Enterprise Sales @ Dwolla

Sales & Account Management (1)

👋 Hi, I'm Katie and I'm looking for a seasoned enterprise sales hunter to join our fast-growing fintech startup. In this high-impact, senior-level individual contributor role, you’ll lead the charge on securing net-new enterprise clients by selling our API-first payments and open banking solutions directly to C-level decision-makers.

Important Note: This role is only for candidates with a successful track record selling payments products (ACH< RTP, Credit Cards, Debit Cards, Acquiring, Opening Banking). Selling to banks or financial institutions is not the same as selling to businesses and merchants. We’re looking for folks who have deep front-line solution selling skills to businesses and merchants. If that’s you, keep reading

The Real Deal About This Role

You’ll be at the forefront of Dwolla’s growth and a key driver in hitting 7-figure revenue targets and opening up new markets. This is a true hunter role for someone who thrives on building pipelines, navigating complex sales cycles, and landing big wins.

Here’s what you’ll be doing:

➡ Identify, target, and manage high-potential enterprise prospects across industries

➡ Own the full-cycle, net-new logo acquisition for mid-market & enterprise (companies with $50M+ in Estimated Annual Revenue)

➡ Strategically partner with channel teams to expand reach and accelerate deal velocity

➡ Deliver compelling ROI narratives for our payments platform and APIs

➡ Collaborate closely with Product and Engineering to surface insights from the field

➡ Keep leadership in the loop with pipeline transparency and clear forecasting

A Day in the Life

At Dwolla, you own your time and your outcomes, no micromanagement here. We expect your time to break down roughly like this:

🟢 50% – Direct sales, active prospecting, and channel partner engagement

🟡 20% – Pipeline management, forecasting, and reporting

🔵 20% – Collaborating with Marketing, Product, and CX teams

🟣 10% – Market research, industry trendspotting, and sharpening your edge

You’ll Thrive Here If You’re…

🤝 A relationship builder: You earn trust and are known for your follow-through. You work well across departments and know how to bring people along for the ride.

📊 Detail-obsessed and data-driven: Salesforce isn’t just a checkbox tool to you; it’s how you guide strategy and spot your next big deal.

🔥 An autonomous hunter: You love the chase. You’re self-motivated, quota-driven, and energized by complex deals with 7-figure potential.

✨ Adaptable and tech-forward: You roll with change, think creatively, and love using modern tools (including AI) to do more with less.

What We’re Looking For

✅ Required:

➡ 5+ years of outbound enterprise sales experience

➡ Proven success selling B2B SaaS or API-first payments solutions

➡ Consistent performance hitting or exceeding 7-figure quotas

➡ Strong understanding of payments flows (ACH, Same-Day ACH, RTP, FedNow, Visa Direct, Mastercard Move, Open-Banking APIs) and fintech landscape

💯 Bonus Points For:

➡ A degree in Business or a related field

➡ Power-user experience with Salesforce and sales analytics tools

➡ You’ve helped shape sales playbooks or contributed to GTM strategies

➡ You thrive in fast-paced environments where change is constant

Salary Transparency & Travel Expectations

Dwolla anticipates the base salary range for this position is between $140,000 - $160,000 and will include an unlimited incentive compensation package and stock options. We want to emphasize that compensation decisions are dependent on a number of candidate-specific factors such as relevant work experience, education, licensure/certifications, geographic location, etc and the salary awarded will be finalized at the time of offer. In addition, Dwolla offers a comprehensive benefits package as outlined below.

Some travel (up to 50%) may be required for prospect meetings, key events, and industry conferences.

What You’ll Get at Dwolla

At Dwolla, we move money, lots of it, through simple, elegant API solutions. We’re a team of smart, driven people building the future of embedded finance.

As a remote-first team, we support your autonomy while providing tools, flexibility, and a culture rooted in ownership and inclusion.

When you join the Dwolla team, you get these great perks:

⭐ Unlimited Paid Time Off (with a mandatory PTO minimum of 5 days every 4 months 😎)

⭐ 12 weeks paid parental leave

⭐ Medical, dental and vision insurance (Health plan options include FSA & HSA options and more…)

⭐ Stock options

⭐ 401k (with 4% company match)

⭐ Long-term disability insurance

⭐ Life insurance

⭐ Summer Fridays (Memorial Day - Labor Day, we sign off at noon 😎)

Our Remote-First Workspace

⭐ Our employees can work from anywhere in the US or from our Des Moines office.

⭐ You can move anywhere in the US and your compensation won’t change.

⭐ Combined with our unlimited PTO, you have the flexibility to enjoy the laptop lifestyle and balance work while traveling.

⭐ We actively support a healthy remote-first company culture by frequently providing both in-person and virtual opportunities for collaboration with co-workers.

⭐ We never miss a beat… by working both synchronously and asynchronously in our day-to-day interactions we’re able to stay full-steam ahead.

⭐ Remote-first home office stipend (and paid parking for our office-loving employees)

❗Please note: While we support a remote-first work environment, we are currently only able to offer employment to candidates who live in the United States

**Some Fine Print**

At Dwolla, we value diversity and hold the core belief that the best teams are built by the inclusion of diverse ideas, experiences, and people. If you require a reasonable accommodation or assistance for any part of the interview and employment process, please contact our HR team at [email protected] and let us know the nature of your request. If offered this position, you will be asked to complete an employment and credit verification authorization form (which allows us to run a background check) as part of our employment process. By submitting this application, you agree that Dwolla may share applicant information with a third party for communication services.

Beware of Hiring Scams: Be wary of fraudulent job postings or communications claiming to be from Dwolla. We will never ask for payment, credit card details, or sensitive personal information (like your social security number or bank details) during our comprehensive interview process. We do not conduct interviews via text message or instant messaging apps. If you are contacted by someone claiming to represent Dwolla attempting to conduct the hiring process through text message or instant messaging apps, it is a scam. All interviews, communications, and legitimate job offers will be initiated through official company channels and verifiable @dwolla.com email addresses. If you suspect a scam, please do not engage and report it to [email protected].

Director – Enterprise Sales

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