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.
What will you do in this role?
The Transformation Lead is a senior technical leader within our Technical Services organization responsible for designing scalable, stable, and efficient customer solutions across our product suite. The Transformation Lead bridges product, engineering, technical implementation, and customer delivery—ensuring that complex configurations, integrations, and pre-GA deployments are architected correctly from the start.
This role is especially critical as we scale to support a 5× increase in implementations, multi-entity PE roll-ups, 100+ pilots, and multiple new product launches. The SA ensures that new products, complex customer scenarios, and emerging implementation patterns are technically sound, repeatable, and aligned with product capabilities.
The ideal candidate is a hands-on problem solver, strong communicator, and systems thinker who excels in collaborative, customer-facing environments.
What will your day-to-day responsibilities look like?
Technical Architecture & Solution Design
Own the technical design for complex implementations, including data flows, integration patterns, and cross-product configuration.
Develop solution architecture diagrams, implementation plans, and integration specifications.
Ensure solutions are scalable, stable, secure, and aligned to best practices.
Advise Implementation Managers and Technical Specialists on edge cases, constraints, and technical approaches.
Pre-GA Product Readiness & Beta Deployments
Lead the technical discovery, feasibility assessment, and implementation approach for new and pre-GA products.
Partner with Product and Engineering to define requirements, identify potential issues, and provide structured feedback loops.
Support and guide beta customers through technical setup and early adoption.
Technical Escalation & Problem Solving
Serve as the senior technical escalation point for API issues, data mapping challenges, workflow design, and integration problems.
Lead root-cause investigations and drive systematic resolution strategies.
Identify patterns across customers to reduce repeat issues and improve product and implementation processes.
Standards, Templates & Repeatability
Create and maintain technical playbooks, architecture templates, integration guides, and configuration standards.
Define technical best practices that improve quality and reduce onboarding time for all customers.
Partner with Enablement to translate technical processes into customer-facing content.
Cross-Functional Leadership
Collaborate closely with Product, Engineering, Implementation Delivery, and Support to ensure alignment on features, capabilities, and rollout planning.
Participate in customer-facing meetings where technical expertise is required—especially for high-value or complex accounts.
Influence product roadmap decisions by representing implementation feasibility and technical field insights.
The ideal candidate candidate for this role:
5–8+ years of experience in Solutions Architecture, Technical Consulting, Implementation Engineering, or Systems Integration—preferably in SaaS.
Strong background designing and delivering integrations (API-based, file-based, or platform-based).
Experience supporting or deploying pre-GA/beta products, or partnering with Product/Engineering on early-stage features.
Experience in data mapping, system configuration, and complex multi-product deployments.
Bonus: Experience supporting multi-entity roll-ups, multi-location deployments, or multi-phase rollout programs.
Additional Skills
Strong technical acumen with the ability to interpret product capabilities, APIs, and data models.
Excellent problem-solving skills—able to navigate ambiguity and design elegant solutions under constraints.
Clear communicator capable of translating complex technical concepts into business-friendly language.
Strong collaboration skills with cross-functional partners.
Ability to think strategically about architecture while remaining comfortable rolling up your sleeves.
Preferable experience also includes:
Experience working in the accounting firm industry
Experience with Monday.com Work Management Software
Experience working with Hubspot and Jira
Benefits and Perks
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.
Other benefits include:
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
Our Values:
Relentless by Design
Owners not Renters
Trust at the Core
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
