Austen DeWolf
91.adewolf@gmail.com · (480) 442-5263 · linkedin.com/in/austendewolf
Director of Engineering | AI-Native Product Builder | Full-Stack SaaS | Founder
Summary
Engineering leader and multiple-time founder with 12+ years building customer-facing software at companies ranging from early-stage startups to public SaaS platforms. I operate at the intersection of product and engineering — equally comfortable defining technical strategy and shaping roadmaps as I am reviewing architecture and shipping code. Track record of building engineering organizations from the ground up, driving measurable business outcomes (31% ARR growth, 100% product line growth, 60% velocity improvement), and leading teams through zero-to-one product launches, platform re-architectures, and an IPO.
Experience
Greater Seattle Area · Remote
- Lead engineering for Hover's largest product vertical — the Estimates organization — generating tens of millions in ARR with strong year-over-year growth; the suite powers estimation, material lists, blueprints, checklists, and direct ordering for construction contractors
- Run a vertically integrated team of 12 engineers spanning full-stack, backend, frontend, mobile, and applied research, owning every product surface from ideation through delivery to the customer's hands
- Drove near 100% growth across multiple product lines while increasing engineering velocity by ~60% through pragmatic architecture and disciplined execution
- Reduced KTLO burden from 43% to 28%, freeing the team to focus on high-impact, customer-facing work
- Shipped AI-powered estimation and trade expansion features, including a centralized regionalized pricing engine that helps contractors maximize margins across markets
- Partner closely with product, design, analytics, research, and infrastructure teams to align engineering investment with business outcomes
Seattle, WA
- Ran product and engineering organizations reporting directly to CEO; joined as first engineering hire and scaled the team from 4 to 20+ engineers while building the product org from zero (0 to 3 PMs)
- Built and executed long-term strategy for product and engineering resulting in 31% increase in annual recurring revenue (2021–2022)
- Owned delivery of Tagboard Interactive (real-time audience engagement), driving a 28% increase in average contract value and $500K+ in pre-launch commitments
- Led evolution of Tagboard Graphics into a real-time, edge-rendered broadcast graphics system handling millions of impressions per second with massive peak-load swings
- Drove platform consolidation of fragmented microservices architecture, reducing infrastructure costs and increasing team capacity for product investment
- Supported fundraising efforts, building the technical narrative and product vision that contributed to Tagboard's $10.3M Series A
- Introduced user research, A/B testing, journey mapping, and prototyping as standards in the product development process
Bellevue, WA
- Employee #97 at Smartsheet, joining pre-IPO and contributing to the company's NYSE listing (SMAR) at ~$1.9B valuation in 2018
- Designed and developed user-facing features across a platform used by millions daily, working closely with product, sales, and support
- Lead front-end developer for the launch of Smartsheet Dynamic View, spanning distributed components and services
- Mentored junior engineers through pair programming, design sessions, and code reviews
Bellevue, WA
- Led technical consulting engagements with Fortune 100 and Fortune 500 customers, designing and deploying scalable enterprise solutions
- Partnered with cross-functional teams of consultants, engineers, and product managers to deliver enterprise-grade applications
- Early contributor to what became the collaborative work management category, helping define product-market fit through direct customer engagement
Anchorage, AK
Founded
Seattle, WA
Co-founded a live podcasting platform for real-time audience engagement at scale. Owned product vision, architecture, and user research from zero to launch.
Seattle, WA
Founded a property management SaaS platform for independent landlords. Led the full lifecycle from customer discovery and product design through development and fundraising.
Skills
Leadership: Engineering Leadership, Engineering Management, Product Strategy, People Management, Managing Managers, Team Building, Stakeholder Management, Hiring Practices
Technical Strategy: Software Architecture, Distributed Systems, Microservices, DevOps, CI/CD, Cloud Computing (AWS), Scalability, Real-Time Systems, Systems Design, SaaS
AI & Data: AI Strategy, Machine Learning, Generative AI, Large Language Models (LLM), Artificial Intelligence
Languages & Frameworks: Python, SQL, JavaScript/TypeScript, React, Ruby on Rails, GraphQL, Full-Stack Development
Education
Bachelor of Business Administration — Double Major, Management & Management Information Systems