Job Description

Location: Oakland Tribune

Shift: Mondays to Fridays, from 7:00 AM to 3:30 PM PDT

Work Arrangement: Hybrid (3 days onsite, 2 days WFH)

Be a Closer. Own the Entire Sales Cycle.

At Skyline Payments, we empower small and medium-sized businesses through smart, scalable payment solutions. We're on the lookout for Account Executives in our Oakland office who are ready to take full control of the sales journey — from prospecting and demos to proposals and closes.

This is the perfect opportunity for SDRs or BDRs who want to take more ownership in the sales cycle and want to level up in a high-growth fintech environment. If you’re a natural communicator, love building relationships, and are passionate about sales, this is your opportunity to be part of a fast-growing FinTech company with unlimited earning potential! We value innovation, continuous learning, and team success — and we want you to grow with us as we scale to new heights!

What Makes You a Perfect Fit

You’re ready to step up and take full ownership of the sales cycle — not just book meetings, but close them too. You’ll thrive in this role if:

• You’ve got hustle. Prospecting doesn’t scare you — you’re proactive, resourceful, and energized by the hunt.
• You’re a natural closer. You know how to build trust, pitch value, and confidently guide prospects to a “yes.”
• You learn fast. Whether it’s a new sales strategy, product detail, or objection — you adapt quickly and use feedback to grow.
• You’re data-driven. You understand the power of merchant statements and know how to build a compelling, number-backed pitch.
• You play to win. You set ambitious goals, hold yourself accountable, and take pride in your results.
• You’re ready for more. Maybe you’ve been crushing it as an SDR or AE — now you want to own deals from start to finish and be rewarded for it.

Responsibilities:

As an Account Executive , you will play a crucial role in identifying and engaging potential clients. Your responsibilities include:

• Self-source leads through outbound prospecting — you’ll initially self-source leads until you continue to transition into more end-to-end sales.
• Own end-to-end sales, including prospecting, qualifying, demoing, and closing deals.
• Deliver tailored, consultative product demos that showcase our payment solutions.
• Collect and analyze merchant statements to build data-driven proposals.
• Negotiate terms and pricing confidently with business owners and decision-makers.
• Track your pipeline in the CRM and maintain detailed, up-to-date activity records.
• Partner with sales leadership to fine-tune strategy and improve performance.

What We Are Looking For:

To be successful in this role, you should have:

• At least 2 years of experience in sales experience in outbound sales as a SDR or BDR and a willingness to source your leads as you transition into more end-to-end sales.
• Strong presentation and negotiation skills — you know how to turn interest into action.
• A track record of meeting or exceeding sales quotas .
• Strong objection-handling and persuasion skills .
• Experience using CRM tools and sales tracking software (preferred but not required).
• The ability to work independently while also collaborating with a team .

About Skyline Payments

Who We Are

Skyline Payments is a trusted FinTech partner with over 10 years in the payments industry, serving thousands of small and medium-sized enterprises (SMEs) with innovative and reliable payment solutions. Our mission is to empower SMBs by simplifying transactions, enhancing cash flow management, and providing exceptional support with our user-friendly software. Over the past decade, we have built a solid foundation and experienced stable growth, and we are now poised to take our expansion to the next level. With ambitious goals and a full-force approach to growth, we’re scaling our impact and continuing to drive value for our clients as we push the boundaries of what’s possible in payment technology.

Why Join Us?

At Skyline Payments, we foster a collaborative, high-energy environment where every team member’s contributions drive our shared success. As we embark on our next phase of growth, our goal is to expand our reach and elevate our impact across the payments industry. We are scaling up operations, exploring new markets, and enhancing our product offerings to meet the evolving needs of small and medium-sized businesses globally.

Joining Skyline Payments now means being part of a transformative period of expansion, where your work will directly contribute to our ambitious growth and help shape the future of payment solutions. We offer significant opportunities for professional development and career advancement, including leadership paths and impactful projects that make a real difference for our clients.

What We Offer

• Competitive Salary and Benefits: We offer a competitive compensation package that rewards your expertise and contributions. In addition, we provide comprehensive benefits including health insurance, paid time off, and other perks to support your well-being.
• Performance-Based Incentives: We recognize and reward hard work with performance-driven incentives, ensuring that your achievements are acknowledged and celebrated.
• Career Growth Opportunities: Skyline Payments is growing rapidly, and with that comes a wealth of opportunities for personal and professional development. We offer paths for career advancement and access to training resources to help you continue to learn and grow in your career.
• Collaborative Culture: Be part of a supportive and collaborative team where your ideas are valued, and innovation is encouraged. You’ll work closely with leaders and peers who are dedicated to driving the success of the business.
• Impactful Work: Join a company that’s trusted by thousands of SMEs and plays a critical role in empowering businesses with cutting-edge payment solutions. Your contributions will directly impact the growth and success of the company and our clients.
• Exciting Expansion Phase: This is a unique opportunity to be part of Skyline Payments’ growth journey, where your leadership and expertise will help shape our future success as we expand our reach and scale our operations.

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