Sam Cleasby started at Abnormal AI as an SDR who had barely used AI beyond opening ChatGPT. Today he is the SDR Enablement Manager, and he builds the AI-driven onboarding that gets new reps up to speed and the development program that prepares them to become Account Executives. A phone call from his mentor on the day he got the role shaped how he approaches all of it.
Learning to Build
As an SDR, Sam found a place where an idea on Monday became something to show by Friday. The idea that grabbed him first was personalization. He wanted messaging that reflected what was happening in the threat landscape that week and spoke to the person on the other end of the call. A better set of templates would not get him there.
So he got access to a ChatGPT Enterprise license, learned how custom GPTs work, and figured it out by doing. The result was The Hook, a GPT that wrote a weekly threat brief and grew into an assistant for competitive intel and objection handling once he loaded it with context on how Abnormal works. At the time, he thought he was solving a problem he found interesting. Looking back, he sees it as the start of a different way of thinking about what he was capable of building.
“A model with no context is generic. A model loaded with the right context becomes something you actually want to use every day.”
A Mentor’s Call
Sam was doing well as an SDR and starting to think about what came next. He found a mentor inside the company who happened to be the SDR Enablement Manager at the time. Their conversations about Sam’s development helped him understand what energized him. Someone he trusted then told him to seriously consider enablement. Sam realized his mentor already did that job.
When the mentor moved into a new internal role, Sam set out to learn everything the job required. He took on enablement side projects, “trying to do the job before I had the job.”
When the call came with the news that he had the job, Sam told his mentor he owed him everything. His mentor answered, “it’s what we do. Make sure to pay it forward.” Sam paused, because he realized his mentor was right. Helping people take their next step is the purpose of the role. The full cycle, from a rep’s first day of onboarding to the day they earn a promotion, is the mission.
“That phone call gave me a lot more than a new title. It gave me a reason to care and give it all I got.”
Building the Path to AE
The SDR to AE development program was already working when Sam and his colleague Sage Howe took it on. Sam wanted to take it further by moving participants closer to the real job. An SDR cannot run live deals, but the program can get close. Sam and Sage rebuilt it so SDRs role play the entire sales cycle, from first meeting through discovery, POV planning, and closing. SDRs also work directly with AEs to prepare for each stage.
“Nobody knows how to sell better at Abnormal than the people who have been doing it at the highest level.”
That belief is why a sales leader plays the prospect. Sam wanted SDRs to learn from the people doing the job instead of consuming resources and hoping the information sticks. Participants have to demonstrate what they know by doing it.
When an SDR earns the promotion, it means they did the work when it would have been easier not to. The team tracks how internally promoted AEs perform compared with external hires and keeps iterating on feedback.
Onboarding Inside Claude
A static learning system gives every new SDR the same experience and hopes it turns out to be relevant. Sam rebuilt SDR onboarding to adapt to the person in front of it. The new version is an AI-driven experience that lives entirely inside Claude.
New SDRs set up Claude Cowork first, since they will use it every day. A 15-day curriculum follows that runs on completion rather than the calendar, so SDRs move forward when they are ready. Each day pairs lessons and practice with a mentor session that has a specific agenda. Mentors and managers can see what the SDR has learned, so live coaching goes where it matters most.
Personalization starts on day one, when the experience asks which segment the SDR belongs to. From there, the competitors they study, the personas they practice against, and the talk tracks they build all fit their world. SDRs can stop mid-lesson to ask a question or practice something again.
SDRs also learn how to use AI while they learn Abnormal. That means the tool they will rely on every day is the one that teaches them the job.
“It is less like an eLearning module and more like an onboarding buddy who knows everything about the job and is available whenever the SDR is ready to learn.”
Fixing the Layer Below
Managers were using AI to pull SDR metrics and often getting wrong answers. A dashboard was the obvious fix. When Sam looked closer, he saw that every manager wants different data at a different level of detail. Since everyone has AI, they can also build whatever views they want on their own. So he asked what the root problem was.
The AI did not know which metrics meant what, which sources to pull from, or which transformations produced the right number. Every wrong answer traced back to that same gap. Sam built the Data Brain, a system that defines every SDR metric, maps each one to the right data source, and routes queries based on what the manager is asking. He found that every manager phrases the same question differently, so he had AI analyze recordings of managers discussing these metrics. The system is built to recognize what each person means however they phrase it.
“Stop solving for the symptom. Find the layer below it that’s causing the symptom, and solve there.”
That approach runs through the rest of Sam’s work. His weeks vary from running SDR Boot Camp in Las Vegas to digging into Snowflake for a conversion pattern nobody has named. They follow one cycle: observe, research in the field and in the data, verify the problem is real, then build. “AI gave me the ability to duplicate myself,” Sam said. He says work that once took a week or two at a large organization now takes him a day.
Paying It Forward
Looking ahead, Sam is most excited to keep learning, because every tool he has built has taught him something he did not know when he started. He also wants to get better at explaining complicated things simply, so the people using what he builds can adopt it and change how they work.
Those goals trace back to the phone call. Sam describes his job as creating the conditions for other people to succeed, rather than enablement in the traditional sense. That is what his mentor did for him. His vision for the SDR function is to make it the talent development factory of the entire company. He spends his days building that environment for the SDRs who come after him.
If you want to build in a place that rewards curiosity and invests in people, explore open roles at abnormal.ai/careers.