Sales Development Representative

Who is Aiwyn and what do we do?

Aiwyn is transforming the way accounting firms manage the entire revenue lifecycle. Backed by top-tier investors like Bessemer, KKR, and Revolution, we’re one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology—and we’re doing it with world-class people, processes, and products.

To learn more, visit our website

About the Role

This isn’t your average SDR job. At Aiwyn, Sales Development is a craft. We’re looking for a sharp, strategic prospector who understands how to build meaningful conversations—not just book meetings. You’ll partner closely with AEs, Solutions Engineers, and Marketing to break into the Top 500 CPA firms. Your success will come from thoughtful account prioritization, creative outreach, multi-threaded engagement, and a long-term approach to relationship-building. This is a role for someone who enjoys the process as much as the results—and wants to become one of the best in the business

You’ll report to the Senior Director of Sales and can work remotely from anywhere in the US.

• Build and execute strategic prospecting plans across a named account list
• Leverage research, trigger events, and industry insights to create high-conversion outreach
• Initiate conversations across email, phone, LinkedIn, and industry events
• Identify whitespace and map key personas across multi-layered orgs
• Collaborate closely with Sales and Marketing to refine messaging and campaign strategies
• Maintain clean, accurate records in Hubspot and support reporting on top-of-funnel metrics
• Stay current on industry shifts, job changes, and firm priorities to keep relationships warm
• Travel up to 20% to conferences, tradeshows, and networking events

• 1–3 years in a Sales Development or similar role (preferably in SaaS)
• Experience with account-based prospecting and multi-channel outreach
• Excellent written and verbal communication skills
• Strong research instincts and curiosity about the customer
• Driven, self-motivated, and comfortable operating independently
• Familiarity with Hubspot, Salesforce, LinkedIn Sales Navigator, Google Suite

• Bonus: Familiarity with the accounting or professional services space
• Bonus: Experience working in an early-stage or rapidly scaling startup environment
• Bonus: Experience working with a multi-product company with the ability to position all products as an integrated platform solution

• The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience.

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
• Remote, work-from-anywhere culture
• Flexible PTO
• World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.
• Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
• 401(k) matching

• Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
• Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
• Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
• Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations

• About us
• Why Aiwyn
• YouTube page

Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.

Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa