Sales Development Representative

Summary

Join Aiwyn, a rapidly growing SaaS company, as a Sales Development Representative (SDR) and become a master of strategic prospecting. Partner with AEs, Solutions Engineers, and Marketing to penetrate the Top 500 CPA firms. You will build and execute strategic prospecting plans, leverage research and insights for high-conversion outreach, and engage across multiple channels. Collaborate with Sales and Marketing to refine strategies, maintain accurate records in Hubspot, and stay updated on industry trends. This remote role offers up to 20% travel and reports to the Senior Director of Sales. Aiwyn offers competitive pay and a work-from-anywhere culture.

Requirements

• 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

Responsibilities

• 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

Preferred Qualifications

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

Benefits

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year
• 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