Senior Director of Implementation - job 1 of 2

Who is Aiwyn and what do we do?

Aiwyn is the fastest-growing software company serving the accounting profession. Founded in 2020, we now work with 100+ of the largest CPA firms in the world. Our “Job to be done”: speed up cash flow, save Partner time, & deliver best-in-class client experiences. We do this by automating day-to-day firm operations with our Practice Automation solutions. Aiwyn is led by serial entrepreneurs with multiple exits and funded by a Top 10 fintech VC.

To learn more, visit our website

About the RoleWe’re looking for a Senior Director of Implementation to lead and grow our high-performing implementation team. In this role, you’ll focus on building strategy, strengthening processes, and guiding your team to deliver seamless, high-quality customer onboarding experiences. You’ll set the vision, coach your team to success, and ensure our customers’ transition from sales to “go live” with confidence, clarity, and satisfaction.

You'll collaborate closely with leaders across sales, customer success, support, and product to make sure every client gets the experience they deserve — one that is smooth, timely, and tailored to their needs. As a fast-paced start up, Aiwyn leaders all roll up their sleeves to help get work done. This role will also focus on  empowering your team, anticipating capacity needs, and creating the playbooks and strategies that make excellence repeatable.

• 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.

• 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.

• 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.

• Champion the use of our project management tools for visibility, consistency, and best-practice adoption across the team.

• 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.

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

• 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