Caleb Hailey
[email protected] • 5032094070 • Portland, Oregon
Work experience
Herd Works Inc https://herd.works/
Founder Full Time Remote
- Building the worlds first static-site generator for iPhone @hypertexting.com
Product Engineer Full Time Remote
- Launched high-performance HTML templating engine @hypertemplates.net
- Developed Golang → Binary XCFramework architecture for shared libs across native apps (iOS, iPadOS), and CLI (Mac, Linux, Windows).
Forward Deployed Engineer Remote
- Launched a 7-figure ARR B2B Shopify Plus integration for a medical device technology startup
- Developed ecommerce-as-code solution w/ Shopify, Stripe ACH, and QuickBooks API integration
- Joined the Shopify Partner Program
Research & Development Engineer Remote
- Reached #1 Paid Safari extension, and #12 Paid App in US iPhone App Store
- Launched iPhone, iPad, and Mac app and website for @themagichighlighter.com
Career Break https://calebhailey.com
Person Full Time Remote
- First time being unemployed >14 days since I was 14 years old!
- Did some volunteering
- Did some traveling
- Played some video games
- Did not think about computers
Sumo Logic Inc https://sumologic.com
Senior Director, Product Management Full Time Remote
- Reported directly to Co-Founder/CTO and CPO
- Integrated acquired technology into flagship platform
- PM lead on Product Led Growth (PLG) initiatives
- Lead advisor on cloud-native initiatives (Kubernetes SME)
- Presented 3x sessions at Illuminate 2021, incl. closing keynote
Sensu Inc https://sensu.io
Co-Founder, Chief Executive Officer Full Time
- Raised over $15M in venture capital & venture debt
- Led Product, Business Development, and Developer Advocacy teams
- Launched cloud-native observability solution used by over 3000 orgs globally
- Recognized as thought leader in OSS, Open Core, Infrastructure as Code
- Acquired by Sumo Logic with 100% staff retention post-acquisition
Automacon https://x.com/automacon
Founder
- Founded and hosted the Automacon 2015 and 2016 tech conferences for Infrastructure as Code practitioners
- Organized keynote presentations from industry leaders, including Kelsey Hightower, Luke Kanies, and Adam Jacob
- Covered conference expenses and generated margins via corporate sponsorships
Heavy Water Operations LLC
President Full Time Remote
- Hired to replace Founder at a 6-month old consulting firm
- Grew team from 4 to 11 employees, 3x revenue in 18 months
- Launched open core software platform (Sensu)
- Pivoted professional services organization to enterprise software business
- Converted Oregon LLC Partnership to Delaware C Corp (for Sensu Inc fundraising)
- Retained 100% of employees in transition from Heavy Water to Sensu Inc
Novitas Data https://novitasdata.com
Director, Product Development Full Time
- Rebuilt product org after cancelation of 3-year vaporware project
- Grew engineering team from 1-10 people while developing new product
- Named inventor, USPTO provisional patent 61/432,500 (contextual search)
- Early adopter of distributed systems design (micro-services architecture)
- Launched innovative SaaS solution that scaled to 6-figure MRR in 90-days
- Notable customers included: Exxon Mobil, Procter & Gamble, Wal-Mart, Home Depot, Lowes, Oracle, and (John) Deere; top 50 law firms: Latham & Watkins, Morgan Lewis & Bockius, DLA Piper, Morrison Foerster, Ropes & Gray; and top consulting firms: Deloitte, PWC, Ernst & Young (US & UK), KPMG, Navigant, and LECG.
Director of Client Services Full Time
- Transformed SMB-class support org into enterprise software support division
- Managed 24x7x365 support for customers in 30+ cities internationally
- Maintained $1M ARR LOB during 72% staff reduction (129% NRR)
- Developed software QA process, increasing release cycle velocity by 425%
- Led sales engineering
Senior Technical Support Specialist Full Time
- Promoted from junior to lead specialist in 12 months (11-person team)
- Technical support lead for proprietary software solution
- Managed software sales fulfillment (physical/virtual appliance provisioning)
- Developed automation solution, reducing config-based support reqs by 90%
Additional experience & education available online https://calebhailey.com
Schweers Technologies https://schweers.com
Technical Project Manager Full Time
- Hired by Schweers from my previous employer (City of Portland)
- Lead Technical Project Manager for North & South America territory
- Developed winning proposals for 6-figure government software vendor RFPs
- Led Sales Engineering efforts for protracted government vendor-selection processes
- Remotely managed team of software & electrical engineers in Meerbusch, Germany
- Managed US Customer Support team
City of Portland https://portland.gov
Parking Code Enforcement Officer Full Time
- Yes, I was a "meter maid". I have some amazing stories. :)
- I met Dean Kaman (RIP) and rode an early Segway prototype (!)
- Wrote technical specification addendum to 6-figure RFP
- Lead SME on Hand Held Citation Issuance System (HHCIS) initiative
- PPOC for RFP-winning vendor (Schweers Technologies)
- Director's Team Award (December 2003, HHCIS initiative)
- Director's Award for Quality (October 2003, HHCIS initiative)
Education
Mount Hood Community College https://mhcc.edu
Student
- Completed Web/Multimedia Management and WebMaster program