Summary
Overview
Work History
Education
Skills
Timeline
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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
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
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)
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
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, VT
05.2013

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

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Kyle Weidman