Kyle Weidman
Bellingham,WA
Summary
GTM and Operations leader with a proven track record of scaling revenue and improving margins in high-growth startups. Experienced in leveraging data and AI tools to automate workflows, uncover business insights, and accelerate decision-making. Expertise in driving product-led and enterprise growth through innovative strategies, operational efficiency, and cross-functional collaboration.
Overview
10
10
years of professional experience
Work History
Head of GTM
Hookdeck Technologies
Remote
08.2023 - 05.2025
- Scaled ARR from $100K to $1.1M (~12% MoM) by overhauling pricing, increasing self-serve conversion from less than 1% to over 3%, and closing major enterprise deals (e.g., Stripe, Mercedes-Benz, Simprosys infomedia).
- Built and maintained powerful Metabase dashboards with AI-assisted insights (mostly Claude-generated SQL) to track key metrics like ACV, NDR, top users, and high-growth potential customers, automating business insights that previously did not exist.
- Partnered cross-functionally with product to design and launch high-impact features—including usage paywalls, countdown trials, event-based email notifications, and pricing unbundling—resulting in increased conversion, upsell, and engagement across self-serve and enterprise segments.
- Improved gross margin from -80% to 75% and helped lead the company to profitability through strategic cost reductions and automation.
Director of Operations
Attentive Mobile
New York, USA
06.2021 - 01.2023
- Led cross-functional collaboration with Product, Engineering, Finance, and Legal to rebuild the Tone Messaging platform within Attentive’s tech stack (Concierge), enhancing GTM alignment, data accuracy, and operational scalability.
- Scaled the support org from 8 to 200+ team members globally, including 8 direct reports, while building foundational systems for hiring, onboarding, and performance management.
- Designed and implemented hiring pipelines, training programs, and compensation frameworks to support rapid growth and global team effectiveness.
- Increased Concierge Gross Margin from 5% to over 55% in 2022, exceeding targets through cost controls, automation, and service model redesigns.
- Drove operational efficiencies that enabled a 700% YoY increase in message volume during peak periods, supporting millions of customer conversations for major ecommerce brands like LG and Reebok.
Operations Lead
Tone Messaging (Acq. by Attentive Mobile)
San Francisco, USA
11.2016 - 06.2021
- Co-founded and scaled Tone Messaging from $0 to $4M ARR, leading to an 8 figure acquisition by Attentive mobile.
- Launched the initial concept (text sales for Fortified Bicycles) and grew it into a SaaS platform for DTC brands.
- Hired and led a 30-person team across engineering, sales, product, and marketing.
Head of Sales
Fortified Bicycle
Boston, USA
04.2015 - 11.2016
- Doubled year-over-year sales and delivered 1,000+ bikes through DTC channels.
- Led online sales strategy, pricing, and performance marketing across Google and social platforms.
Education
Bachelor of Science - Business Economics
University of Vermont
Burlington, VT05.2013
Skills
- AI & Data Tools: Looker, Metabase, SQL, Clay AI, AI Agents tooling, Claude, ChatGPT, Zapier AI, Makecom, n8n
- Productivity & Collaboration: Notion AI, Jira, Figma, Productboard
- Customer & GTM Platforms: Salesforce, HubSpot, Customerio, Apolloio
Timeline
Head of GTM
Hookdeck Technologies
08.2023 - 05.2025
Director of Operations
Attentive Mobile
06.2021 - 01.2023
Operations Lead
Tone Messaging (Acq. by Attentive Mobile)
11.2016 - 06.2021
Head of Sales
Fortified Bicycle
04.2015 - 11.2016
Bachelor of Science - Business Economics
University of Vermont