Coachable AI

Coachable AI is my new favorite sales training tool. Send me your email if you’re interested in testing it!

Many told me I was crazy to build something in sales training & coaching. Everyone was betting on AI replacing human sales reps and urging me to pivot into that space, but I had no interest. I started Coachable AI because I was frustrated with the sales tech available to my teams.?None of it actually helped improve their skills or get better at selling, no matter how much was promised. "Sales coaching" had become a buzzword for "sales insights". Great in theory, but missed the mark to turn them into action. So I went all-in on one hypothesis: sales reps want to get better, but sales leaders don't have the time. It began as a sort of passion project, teaching myself to code and learning about AI, to see if I could build something I wish I had as a sales leader. The early conversations with investors were tough, "AI is going to automate everything", "Sales roles won't exist, so it's a shrinking market" or "Focus on efficiency, not effectiveness". I'd be lying if I didn't say there were times I thought they might be right. I questioned if I was just in denial about a coming exodus of the sales rep. But my bet was simple: The future would demand MORE from sales reps, not less. Seeing a16z now predict a "golden era of sales", where AI handles the admin work, and lets reps focus on high-touch, consultative selling feels like the tides might slowly be shifting. Not replacing sales reps, but accelerating the need for more highly-skilled ones. Because unsurprisingly, humans want to buy from humans, and the more productive & well-trained your reps are, the more you can scale revenue.

Sales training often feels disconnected from reality. Generic role-plays. Prebuilt scenarios. One-size-fits-all sessions. We’re changing that. Now, you have the power to create simulations that match your exact target market. All in just minutes, no lengthy onboarding, no integrations needed. With Custom Personas, tailor your practice sessions to buyers who actually resemble the ones you’re selling to.. Because on-demand practice with the right personas matters: - The Founder with 6 employees thinks differently than the Founder with 60. - A Sales Manager has different priorities than their VP. - An SMB deal brings different challenges than Enterprise. Take control of your simulations and personalize every detail, from industry to location and beyond, so your practice feels as real as it gets. The future of sales training isn't generic - it's personal. Your first 5 simulations are always free, so give it a try today!

To demo or not to demo, why does this question even come up? Every few weeks I see another post: "NEVER demo on your first call!" This typically tells me that the person posting doesn't actually understand sales. Demos are perfectly fine on a first call...if that's what your buyer needs in that moment. The best salespeople I've worked with don't follow strict rules, they follow their intuition. They pick up on the subtle cues during discovery: - When someone needs to "see it to believe it" - When a quick demo beats 20 minutes of explaining - When a prospect is giving you those "I need to visualize this" signals We don't talk enough about the power of sales intuition because it's hard to replicate or train. The ability to read the room, pick up on conversational nuances, and know exactly where to take things next. This is where good sellers become truly great. Sales isn't won by following a perfect script or playbook. It's about giving each buyer what THEY need to move forward, when THEY need it. Even if that means breaking a "rule" or two

SDRs, AEs, and Sales Leaders on the search for your next role, check out these fresh job postings and land your next gig before the holidays! ?? SPATE - SDRs - Spate leverages data science to predict the next big consumer trends in beauty, personal care & food. Brands waste over $200BN every year due to product launch failures and inventory waste, but tapping into interesting shifts in consumer behavior empowers them to stay ahead in a fast market. Infisical - Enterprise AE - On a mission to make secure software faster, cheaper, and more enjoyable to build, Infisical is the top open source secret management platform for developers. Already processing over 100M secrets per day, join to work with customers like Hugging Face & Delivery Hero. Moonvalley - VP of Sales - Moonvalley is on a mission to build the platforms where the first generative Super Bowl ads and Oscar winning movies will be created. Powered by the most capable video and image models in the world and led by a founding team with deep experience in AI, join to build out and scale the revenue org expansion into retail & e-commerce.

Simone Biles Lebron James Katie Ledecky Lionel Messi Coco Gauff Lamar Jackson Sydney McLaughlin-Levrone Scottie Scheffler Caitlin Clark Connor McDavid All of these top athletes compete in different sports with entirely different processes, but the one thing they all rely on? Practice 90% of their week is spent training, all leading up to the actual competition. Every day is spent in the gym - making mistakes, boosting confidence, training their weaknesses, and building muscle memory to prepare for any situation. Even being at the top of their game, they don’t just step in unprepared and wing it. Isn’t it time we treat sales the same way? Buyer expectations are changing, sales is getting harder, and we’re well past the days when an average rep could still hit quota. Stop jumping right into the arena with real prospects, without warming up and having a practice routine. The sales reps and leaders who build the habits today, will be the elite ones on top tomorrow. Tell me I'm wrong -- Coachable AI provides the risk-free practice environment through personalized role-plays for cold calls and discovery meetings, with immediate feedback and coaching. Try for free and experience your first simulation in 2 minutes!

Two products had the perfect answer for what I needed, but I didn't buy either one. Last week, I urgently needed a solution to create a tailored demo with personalized content, for a prospect. It didn't need to be fancy, just wanted to show off some of Coachable AI’s features, tailored to their content and scoring framework. A quick Google search gave me two products that checked all the boxes. Company A: - Great demo video - No-code process - Free trial offered, without the no-code option ($600+/month to access) Company B: - Great demo video - Met all of my needs - No free trial, demo available the next day Even though both companies had what I needed, urgency was key for me in the moment. Which one did I go with? Neither. I used Figma for the first time, and was able to do exactly what I wanted. It took less than an hour and it was free. Many buyers are in a similar boat - they don't know they need you until they feel a pressing pain. Make it easy for them to solve it, otherwise there's always going to be a competitor or simpler solution that does.

Let's get you hired! If you're currently searching or just browsing, here's some open sales roles posted this week for SDRs, AEs, & Sales/Revenue Leadership. Links in the comments to apply directly! FirstIgnite?- SDRs & AEs - AI-powered platform designed to help researchers and university academics effectively market their innovation & discoveries, connecting them with industry partners for collaboration. Trusted by over 100 scientific organizations, join FirstIgnite to be in the forefront of how discoveries make it from lab to market. Pilot.com?- AEs & Leadership - On a mission to help startups & SMBs grow and flourish, Pilot is building the future of the financial back office. Through their bookkeeping, tax and CFO services, you’ll get the opportunity to sell into some of the most exciting companies out there, customers they’ve supported include OpenAI, Scale, Airtable & Lattice. Stable?- AEs - Streamlining and simplifying the process for any business on the internet to have an HQ through mail operations and registered agents. Over 4000 companies like Gitlab, Glassdoor, and Indiegogo are already using Stable to automate their mailroom and act as their permanent business address with the IRS, state, and vendors. Sendbird?- SDRs - Communications platform providing APIs for chat, voice, video, and omnichannel messaging, enabling businesses to create seamless and engaging user experiences. Already powering over 4,000 apps around the globe, Sendbird is on a mission to drive more connections in a digital world. Prelim?- AEs - Providing a white-labeled, no-code platform that helps financial institutions digitize the entire business customer journey, from onboarding to servicing, enhancing operational efficiency and user experience. Prelim is building the next gen digital banking experience with customers totalling $5T in assets?

92% of sales reps say that AI has improved their efficiency. Effectiveness? That's another story. That recent quote/stat from Gong hit home. I experienced the initial boom of AI in sales from the buyer side, when I was Head of Sales. I took countless meetings to see what the hype was about and kept leaving with the same thought: "Sure, these tools might make the team more efficient, but do they actually make us more effective?" Everyone was optimizing for efficiency, but with Coachable AI, I knew there was a gap in effectiveness—helping reps improve their skills, conversion rates, and performance. Probably because these weren’t just challenges I heard about, or witnessed from afar. They were problems I faced every day, as a sales rep and leader, over the last 10 years. From the fear of picking up the phone in my first SDR job, and sales slumps where I couldn't book a meeting to save my life. The countless days where I thought hearing another "No" from a prospect would make me quit sales forever, and having great mentors and managers to talk me out of it. From celebrating every milestone along the way from $0 to $50M in ARR, but knowing that the road was bumpy, difficult and plenty of mistakes were made. I think that's why messages like these from users hit home. It's not just "Cool, another happy customer ?" It's getting genuinely excited to share in their wins, because I know how hard the job is and the work it takes to be successful. Don’t get me wrong, efficiency in sales is critical. But once your workflows are optimized, how effective are you going to be with your additional time?

Job searching is a full-time job on its own, so take a look at these open SDR & AE roles, all posted this week! Upcoming interview? Check out how Coachable AI can help you prepare for the mock call role-play step! Links in comments to apply! HOKALI - AE - Hokali simplifies the booking and management of after-school programs and camps, connecting schools with high-quality, pre-vetted vendors. Join to be part of a mission to enhance children's learning and fun through engaging activities, trusted by over 100 schools and districts across the U.S. Tavus - SDR - Tavus is pioneering AI video enabling developers to create realistic digital twin experiences for video generation and real-time conversations. You'll be at the forefront of humanizing AI interactions and helping to redefine how brands engage with their audiences through personalized, immersive video content. Morty - AE - Morty provides the infrastructure and technology for loan officers & brokerages to efficiently start, manage and streamline their business operations. With over $2B in mortgages serviced, join the mission in empowering professionals to grow their businesses with innovative solutions and access to a wide network of lenders. Happeo - SDR - Happeo is a next-generation intranet platform unifying knowledge management and internal communications, enabling teams to collaborate seamlessly and access information efficiently. Reporting into the marketing team, you’ll always know which messaging and ads are running, while empowering employees to thrive in a digital environment. Medely - AE - Medely is an online talent marketplace connecting nurses and allied health workers, with flexible positions quickly and efficiently. Join to be part of a mission to empower healthcare workers with flexible scheduling options and competitive pay, all while enhancing patient care across the healthcare system.