Lindsay Henry

I help businesses build AI they actually own, tailored to them, transparent, and focused on their outcomes.

San Diego4.3k followers

AgentsOS

ex-RadarFirst

ex-Outreach.io

I have spent my career building the engine that turns a good product into real revenue. The sales motion, the process, and most of all the team.
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I have done it inside companies finding their first playbook and inside companies rewriting one they had outgrown, and if there is a single throughline, it is that I build, and I help businesses change when the moment calls for it. This is one of those moments. AI is forcing nearly every company to pivot, and the ones with an existing customer base and real trust in the market have a genuine advantage, if they move well. That base is worth more in a transition, not less. But capitalizing on it takes expertise to maneuver the pivot without breaking what already works, and that is the kind of work I have done at every stage I have operated in. The part I am proudest of is the teams. Hiring people, betting on them, and watching them grow into a group that does the best work of their careers and actually wants to stay. You can build pipeline and hit a number in a quarter. Building a team that trusts each other and sticks together is the harder thing, and it is the thing I care about most. The other is the customers. I have never been interested in the one and done deal. The relationships that lasted years, where a customer calls me first because they know I will tell them the truth, are what I am most proud of carrying from one chapter to the All of that led me to StartupOS, where I lead go-to-market for our AI-native services solution, AgentsOS. It is the clearest expression yet of how I have always believed this work should be done: build the right thing alongside the customer, make it theirs, and stay focused on their outcome. The rest of that story is in the role below.

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GTM Index

AGENTSOSJOB
1. GTM Lead, Founding Team
  2M
SQLDBM - ONLINE DATA MODELING TOOLJOB
1. VP of Sales
  1Y 11M
RADARFIRSTJOB
1. Dir of Sales
  6M
YEXTJOB
1. Dir of Enterprise Sales
  2Y
KANDJIJOB
1. Founding Enterprise Accoun…
  8M
INTRICATELYJOB
1. Strategic Sales Advisor
  9M
2. Head of Sales
  1Y 3M
OUTREACH.IOJOB
1. Founding Enterprise Accoun…
  1Y 1M
DATANYZE INC. (ACQUIRED BY ZOOM INFO)JOB
1. Founding Account Executive
  3Y 8M
FLIPTOP (ACQUIRED BY LINKEDIN)JOB
1. Founding Account Executive
  1Y
ACTUATE CORPORATION (ACQUIRED BY OPENTEXT)JOB
1. Sales Development Represen…
  1Y 2M

Job: RadarFirst — Director of Sales · 2024-01 – 2024-07 — RadarFirst’s innovative governance, risk and compliance (GRC) software solutions are trusted by enterprises and organizations to reduce risk and simplify obligation decisioning. The award-winning Radar® technology automates assessment processes to help companies meet time-bound response requirements and delivers transparent notification obligation decisioning against global data breach laws, as well as compliance and cyber regulations. With RadarFirst, organizations can define, streamline, and scale decision making in a consistent, objective process.
Job: Outreach.io — Founding Enterprise Account Executive · 2017-12 – 2019-01 — Outreach was already a fast-growing success in the sales engagement category when they brought me in to help crack the enterprise. Moving upmarket is its own discipline. Bigger accounts, more stakeholders, longer cycles, and procurement and security reviews that a mid-market motion never prepared you for. They hired people who had already done that kind of complex, multi-threaded enterprise selling, and that was the background I brought from founding and early-stage roles where I had built enterprise motions from the ground up. I was a top performer from the start. I set a company record for most closed in my first month and ranked as a top seller during my time there, helping prove that t…
Job: Intricately — Strategic Sales Advisor · 2020-04 – 2021-01
Job: Actuate Corporation (acquired by OpenText) — Sales Development Representative · 2012-01 – 2013-03 — Specialize in the Financial Services sector and Fortune 1000 Companies Proactively generate new business leads via Internet prospecting/research Manage and track all correspondence, leads, and sales through Salesforce.com Conduct high-level phone calls to middle/senior level executives to determine their needs and fit with company products. Understand products, competition, strengths and functionality in sufficient depth to qualify prospects by phone Promote monthly seminars, register prospects and follow up with attendees Research to gain necessary account information and formulate account strategies Work with Marketing to determine which market segments are producing the most qualified le…
Job: AgentsOS — GTM Lead, Founding Team · 2026-06 – present — Anyone can build an AI agent now. The difference is knowing which ones a business actually needs, building them right, and keeping them that way, and that comes down to expertise. We work alongside our customers to develop and build exactly what their business needs, on top of how their best people already work. Then we make sure two things are true that usually are not: the customer owns their agents, and they can see inside them. Most AI is a black box you rent. Ours is yours, and it is transparent. That ownership is what protects a company over time. People leave. Models change. New capabilities show up every month. Because our customers own their agents and we bring the expertise to k…
Job: Fliptop (acquired by LinkedIn) — Founding Account Executive · 2013-03 – 2014-03 — Founding Account Executive at Fliptop, a predictive analytics company later acquired by LinkedIn. This was applied machine learning years before AI became the thing every company talked about. We built predictive models that scored and prioritized accounts so revenue teams could focus on the buyers most likely to convert, the same logic that powers a lot of AI-driven go-to-market today, just years ahead of the curve. As the founding AE, I built the sales motion from nothing and carried the harder version of the job: selling a sophisticated, model-driven product to buyers who were not yet used to trusting an algorithm to tell them where to spend their time. That meant teaching the market, n…
Job: Yext — Director of Enterprise Sales · 2021-09 – 2023-09
Job: Datanyze Inc. (acquired by Zoom Info) — Founding Account Executive · 2014-04 – 2017-12 — Joined as the 5th employee and first Account Executive, building the sales motion from the ground up: pricing, packaging, messaging, positioning, competitive strategy, and the creative plays that actually moved the product. Also helped build and scale the sales team as the company grew. Grew ARR from $0M to $9M and averaged 135% of quota. Top AE in 12 of 14 quarters. Logos acquired include Okta, Salesforce, Symantec, Adobe, Oracle, Marketo, Criteo, AOL, and CA Technologies. One of the things I am proudest of: we started as a tool sold to CROs and revenue leaders to help them identify their best accounts to target. I opened up an entirely new motion by selling our data as raw files, helpin…
Job: Kandji — Founding Enterprise Account Executive · 2020-11 – 2021-07 — Kandji is an Apple device management (MDM) solution built exclusively for IT teams at organizations that run on Apple. Kandji is a modern, cloud-based platform for centrally managing and securing your Mac, iPhone, iPad, and Apple TV devices, saving IT teams countless hours of manual, repetitive work with features like one-click compliance templates and 150+ pre-built automations, apps, and workflows.
Job: SqlDBM - Online Data Modeling Tool — Vice President of Sales · 2024-05 – 2026-04 — Inherited hundreds of customers across every price point in the market, no playbook, and a team that needed to be rebuilt. The business had been built with an SMB model. The opportunity was Enterprise. Within 60 days, diagnosed what was broken and developed a full go-to-market pivot strategy. Six quarters later, the results spoke for themselves. Built every revenue function from the ground up- SDRs, AEs, SEs, CSMs, AMs, Sales Ops, AI Deployment, Onboarding, and Renewals. Zero voluntary attrition. Every person was put in a position that matched their strengths, given the support and trust to do their best work, and empowered to deliver the biggest impact for customers. That investment sho…
Job: Intricately — Head of Sales · 2019-01 – 2020-04 — Intricately offers a data set that most marketing and sales teams never knew existed. Companies that sell digital products that still use firmographic data to uncover their total addressable market are missing the most important factor -- a prospect’s investment in digital spend. Our data allows organizations to truly discover who their top target accounts are and disqualify companies who aren’t a good fit before investing your team’s time and money. Customers like AWS, Google, Fastly, and Verizon redefine their target accounts, enhance current scoring/propensity models, identify new markets/verticals and much more.
School: Evergreen Valley College — Associates Degree, Liberal Arts
School: Evergreen Valley College — Associate of Arts, Liberal Arts and Sciences/Liberal Studies

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Lindsay Henry

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