Aiwyn

Role Description As part of our Customer Support team, the Customer Escalation Manager at Aiwyn is responsible for overseeing, coordinating, and resolving high-impact and complex escalations identified through internal monitoring or customer channels. This role ensures escalated issues are prioritized and resolved efficiently, customers are communicated with transparently, and internal teams collaborate effectively to prevent recurrence and drive long-term improvements. Investigating escalations at Aiwyn requires operating within a highly integrated technical ecosystem. This work includes: - Executing database queries - Analyzing user session replays - Reviewing application and network logs - Performing transaction-level investigations to identify root cause - Tracing source data from external systems through multiple integrations into Aiwyn’s database - Diagnosing issues related to DNS configuration and mail servers - Understanding complex interactions with third-party systems including third party practice management systems, SafeSend, and Outlook Successful candidates are comfortable navigating ambiguity and synthesizing data across systems to drive resolution. Qualifications - 3–5+ years in escalation management, technical support, customer success, or related fields - Proven experience managing customer-impacting incidents in a production SaaS environment, including use of incident management tooling (such as incident.io) to coordinate responders, manage timelines, and drive post-incident actions - Curious and data-driven mindset with experience analyzing trends and reporting on outcomes - Strong ability to work with datasets, metrics, and reporting to debug issues, assess customer impact, and drive data-informed escalation and post-incident decisions - Familiarity with support platforms and issue tracking tools (e.g., Zendesk and Jira) - Clear customer and internal communication skills, with the ability to simplify complex technical concepts - Excellent prioritization and organizational skills Requirements - Familiarity with SaaS platforms and cloud-based software solutions - Strong understanding of accounting principles and experience with accounting or accounts receivable software 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 - including 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

• Partner with GTM leadership (Sales, Marketing, CS, and Alliances) to define and execute integrated campaigns that drive awareness, adoption, and pipeline growth. • Lead product storytelling and positioning across one or more product lines, articulating how Aiwyn helps firms modernize, scale, and deliver better client experiences. • Own the go-to-market strategy for major product launches, including messaging, enablement, content, and performance reporting. • Collaborate closely with demand gen to align messaging, content strategy, and campaign execution around key firm segments and revenue goals. • Build and maintain enablement programs that elevate how Sales and CS articulate value across the full Aiwyn platform. • Drive customer marketing initiatives including references, case studies, and upsell/cross-sell strategies across product lines. • Identify product adoption metrics, partnering closely with Sales, Customer Success, and Product to understand usage trends, identify friction points, and develop strategies that accelerate activation and retention. • Educate and evangelize PMM best practices across the organization, helping peers and cross-functional partners understand how product marketing drives business impact and how to collaborate effectively. • Mentor and coach other PMMs, helping to build structure, consistency, and scale within the team as Aiwyn continues to grow.

• Build the systems firms run their business on • Work in the trenches with the domain experts • Build and extend the APIs that Aiwyn, firms, and partners build on top of • Take projects from spec to ship to scale

• Build the systems that move money reliably • Work in the trenches with the domain experts • Build and extend the APIs that Aiwyn, firms, and partners build on top of • Take projects from spec to ship to scale

• Own Payments strategy and the P&L. Set the direction for Aiwyn's flagship product and own the results. • Own the roadmap. Decide what we build and in what order, prioritize ruthlessly, and ship what firms actually adopt. • Own our banking and payments partnerships. Build and manage the relationships that power processing and money movement. • Go deep with customers. Sit with firms, own the most important accounts, and turn what you learn into product wins and retention. • Partner cross-functionally to execute. Work with a dedicated execution PM, engineering, and design to ship, and with sales, CS, and marketing to bring it to market.

• Own the end-to-end success of complex, multi-product customer implementations. • Develop and maintain comprehensive program plans that coordinate multiple workstreams, phases, and product deployments. • Ensure all implementation activity stays on schedule, on scope, and aligned to delivery objectives. • Lead the Advanced Implementation Delivery Trio — Solutions Architect and Implementation Engineer — driving alignment and accountability across each function. • Serve as the primary delivery leader for enterprise customers throughout the implementation. • Facilitate executive-level conversations on program progress, key decisions, and delivery strategy. • Own scope integrity across the program — identify scope creep early, manage change control, and communicate tradeoffs to both the customer and internal leadership. • Partner closely with the Solutions Architect to ensure the proposed solution is being executed as designed. • Establish and own the operational rhythm of the program — weekly syncs, milestone reviews, status reporting, and executive readouts.

• Lead the leaders. Coach and develop EMs across infrastructure, foundations, tax engine, implementations, and productivity. Hire when the bar requires it, performance manage when it doesn't, and build a leadership team that can scale. • Own the operating model. Define the rhythms, metrics, and standards that make the org legible and accountable, including cycle planning, change management, design review, incident response, and on-call quality. • Set technical direction. Partner with your engineers, EMs, and anyone else with strong opinions on the multi-year evolution of the tax engine, the ingestion and normalization pipeline, and our core infrastructure on GCP. • Hold the bar on operational excellence. Get us to daily deploys. Push incident response toward root cause. Build the metrics and forums that make execution legible and force the right conversations. • Partner across the company. Work shoulder to shoulder with your peer product leader on platform, with the product engineering org, with support, and with GTM. Earn trust by execution and by making other teams demonstrably better.

• Own the technical evaluation end-to-end. Lead technical discovery, feasibility assessment, and solution architecture across the pre-sale cycle. You're the definitive answer to "can we do this, and what will it take?" • Design systems-level solutions. Translate firm workflow requirements into integration blueprints spanning APIs, webhooks, data migration, ETL, and SSO — and assess feasibility without pulling in Engineering for every question. • Produce contract-quality scoping documents that Delivery Leads can execute without re-discovery. Your work product sets the implementation up to succeed. • Run executive rooms. Build credibility with firm-side CTOs, COOs, and partners and shape deal strategy alongside our AEs, influencing evaluation criteria and accelerating technical buyer trust. • Uncover what firms actually need including what they can't articulate and synthesize findings into designs, timelines, and constraints. Knowing when to say no is part of the job. • Build the playbook. Turn ad hoc wins into a reproducible structure that reduces ambiguity for everyone around you. • Carry field signal back to Product with specificity patterns across engagements, not one-off feature requests. • Show up in person. On-sites and joint sales calls are a material part of this role, and you genuinely enjoy them.

• Take problems from concept to shipped. • Build natively agentic workflows. • Set up the loops. • Run prototypes with real users. • Partner widely. • Translate frontier-model capability into product.

• Manage and grow the team. • Own the tax engine roadmap with your PM and tax leads. • Build the system that builds the engine. • Work in the trenches with the tax experts. • Operate cleanly.