the gtm engineer Rebuilding GTM with AI at Monday.com with Oran Akron, Head of AI GTM at Monday
Oran Akron is the VP of AI GTM at monday.com, where he leads a new internal team focused on rebuilding go-to-market processes with AI agents.
Oran joined monday.com in 2018 when the company had ~100 employees and just five sellers. Since then, he’s helped scale the revenue org to over 1,000 people across sales, customer success, marketing, and partnerships while growing the RevOps team from one to more than 80. About six months ago, after conversations with monday.com’s new CRO about the future of GTM, Oran decided to step away from RevOps and incubate something new.
His team operates like a startup inside Monday, moving fast and shipping agents that are already handling the majority of inbound leads, expanding into new languages and markets, powering outbound research, and surfacing product usage signals that trigger sales engagement.
In this podcast, we discuss:
* Why Oran decided that AI was going to fundamentally change go-to-market and why he started a new team inside Monday dedicated to rebuilding GTM processes from scratch with AI
* Why improving the top of the sales funnel was the first problem Oran’s new team tackled and how AI agents now handle inbound qualification and meeting booking across multiple languages
* How Oran’s team built an outbound agent that automates account research and generates personalized recommendations for reps, while preserving their autonomy over how to use it
* The importance of monitoring AI agents in production and how Oran set up dashboards, failure tracking, and observability to scale with confidence
* What Oran learned about change management, internal branding, and gamification to get a 3,000-person org to embrace AI agents
Episode highlights:
* After seven years of building and leading RevOps, Oran felt that if he had to build Monday’s sales org today, he would do it much differently. With support from Monday’s CRO, they agreed to have Oran step away from RevOps and incubate a new team within Monday focused on rebuilding GTM processes from scratch with AI.
* Oran’s new team started with inbound lead handling. The team tested against cohorts of their best-performing human reps, scaling only after results were equal or better. The results matched or exceeded top rep performance, and Oran’s AI now handles the majority of inbound leads, conducts real conversations that run five minutes or longer, qualifies prospects, and books meetings directly on AE calendars.
* They built an outbound agent to listen to everything on the web, from podcasts to financial reports to LinkedIn activity, and synthesize that research into personalized account plans. The agent then recommends which department to target, why to start there, and how to position Monday’s offering based on what’s happening at the account. Importantly, reps retain full autonomy over how they use the output, as Oran doesn’t believe in forcing a playbook on them.
* Oran treats his agents like an engineering system that needs to be closely monitored. His advice for others implementing AI agents in GTM is to start by tracking the same business performance metrics used for human reps, then layer on engineering-style observability to catch where things break
* Oran explains that change management was the biggest organizational challenge he faced in his new role. The most effective approach combined top-down communication about the future of AI in go-to-market, gradual rollouts rather than all-at-once deployments, and a deliberate effort to make the agents feel exciting rather than threatening.
Where to find Oran:
Transcript details:
(00:00) Intro
(03:06) Oran’s monday.com journey
(08:06) Why Oran pivoted to focus on AI in GTM
(11:07) Prioritizing top of funnel wins to build trust in implementing AI across the org
(14:19) How Amanda, the inbound agent, qualifies leads and books meetings in two minutes instead of 24 hours
(15:42) Expanding into new language markets without hiring local teams
(18:42) The AI ecosystem behind the agents and why Amanda was rebuilt four times in six months
(20:40) Monitoring, guardrails, and treating AI agents like an engineering system
(24:22) The next most impactful use cases beyond inbound
(24:39) The outbound agent that researches accounts across the web and builds personalized account plans
(26:35) Product usage signals and identifying intent in real time to trigger sales engagement
(27:36) Giving reps autonomy over the AI output rather than forcing a single playbook
(29:26) How the team serves information through the CRM and monday.com’s own AI tools
(30:38) Change management, over-communicating the strategy from the top, and other strategies to drive adoption
(35:29) How AI changes what’s required from salespeople and why relationship building becomes more important
(40:18) Why moving fast and launching before perfection is a worthwhile tradeoff
(43:29) Reinventing PLG by understanding user intent in real time instead of distributing leads 24 hours later
(45:46) Favorite tools, growth campaign, and wrap-up
For inquiries about sponsoring the podcast and to recommend any guests, email noah@thegtmengineer.ai
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thegtmengineer.substack.com