Resume

A snapshot of where I've been and what I've built.

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

Senior Engineering Manager, Product Engineering · HOVER Inc.
Jul 2023 – Present

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
Director of Engineering · Tagboard
Jan 2020 – Feb 2023

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
Senior Software Engineer · Smartsheet
Jun 2018 – Jan 2020

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
Solutions Architect · Smartsheet
Oct 2016 – Jun 2018

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
Software Engineer · Resource Data Inc.
Jun 2014 – Oct 2016

Anchorage, AK

Founded

Jan 2021 – Jun 2023

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.

Flatly flatly.com
Jan 2016 – Dec 2018

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

University of Alaska Anchorage2009 – 2014

Bachelor of Business Administration — Double Major, Management & Management Information Systems