Senior Director of Implementation

Summary

Join Aiwyn, a rapidly growing software company serving the accounting profession, as a Senior Director of Implementation. Lead and grow a high-performing implementation team, focusing on strategy, process improvement, and seamless customer onboarding. Set the vision, coach your team, and ensure smooth client transitions. Collaborate with sales, customer success, support, and product leaders to deliver exceptional client experiences. This role also involves empowering your team, anticipating capacity needs, and creating strategies for repeatable excellence. Aiwyn is a fast-paced startup where leaders are hands-on, contributing to the work. The company offers competitive pay and a chance to solve challenging problems alongside other high-achievers.

Requirements

• Passionate about building and leading high-performing teams
• Naturally curious — you dig deeper when something doesn’t work as expected
• Thrive on solving complex challenges and finding better ways to do things
• Relentless in your pursuit of excellence for the client, the team, and the business
• Courageous in voicing ideas, sharing feedback, and driving change
• Skilled at building trust through empathy, transparency, and follow-through
• Able to balance ownership of results with openness to feedback and collaboration
• 7+ years leading implementation teams for SaaS solutions, ideally in an early-stage or growth company
• Proven track record in strategic leadership — building scalable processes, forecasting capacity, and leading through change
• Strong project management skills with the ability to oversee multiple implementations at once
• Excellent communication and problem-solving skills across all levels of an organization
• Familiarity with SaaS integrations and — ideally — experience in tax, accounting, or professional services

Responsibilities

• Lead, mentor, and inspire a growing implementation team, fostering a customer-first mindset and a culture of collaboration, transparency, and accountability
• Conduct regular one-on-one meetings and performance check-ins to develop skills, encourage growth, and keep the team engaged and motivated
• Set clear goals for the team and individuals that align with Aiwyn’s strategic objectives, and track progress toward those goals
• Forecast resource needs and balance team capacity to ensure timely delivery across multiple, concurrent implementations
• Refine and expand our implementation playbook and processes, creating scalable, repeatable methods that improve quality and efficiency
• Monitor implementation quality using client feedback, internal metrics, and performance data — then turn insights into actionable improvements
• Partner with sales to ensure smooth handoffs and create tailored implementation plans that match each client’s needs
• Work with product, support, and customer success teams to remove roadblocks, resolve escalations, and continuously improve the onboarding journey
• Promote proactive communication with clients and internal stakeholders to keep projects visible, transparent, and on track
• Oversee hiring, onboarding, and training for new implementation team members, ensuring they are set up for success from day one
• Champion the use of our project management tools for visibility, consistency, and best-practice adoption across the team

Preferred Qualifications

• Background in the accounting firm industry
• Experience with Monday.com , HubSpot, Zendesk, and Jira

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