5 Strategies for Hiring Sales Leaders Who Can Sell AI Software
We predict that 2026 will be the year of monetising AI and given it takes on average 3 months to hire the right person, now seems like a good time to start thinking about how to find the star performers.
Selling AI products is hard, because the market is in such an embryonic stage.
The main problem is that there’s a limited pool of people who have actually successfully sold AI before.
Ok - we know there are a Top Guns working in Anthropic and Google etc… but realistically they’re going to blow your budget and be impossible to move if they’re really that good.
So how do you hire your first go-to-market leader for your revolutionary AI product?
Here are my 5 tips.
Hire a software sales expert - from non AI sectors.
This seems obvious, target a successful CRO, VP Sales, Sales Director or Senior AE with a strong interest in AI and a track record in Enterprise software sales.
Someone who’s experienced with long cycles and multiple stakeholders.
Hire a person who’s already navigated these complex environments with a strong sales process, methodology and deep relationships.
Non-AI sectors who’ve sold deep tech, data, analytics or cybersecurity. These are transferable sector skills.
Also, remember to invest in technical training for your sales team.
2. Consider a Chief Growth Officer from the scaleup sector.
One person to lead Sales & Marketing.
AI branding is fuzzy. Buyers are cautious. Someone needs to turn hype into income. The ideal profile could have run both revenue and marketing before and be capable of developing new revenue streams.
People who’ve lived the chaos of a scale-up know how to thrive when things break, shift, and evolve overnight. They’re adaptable, and bold enough to turn uncertainty into growth. Exactly the mindset you need to push an AI product to market success.
3. Hire a Technical Sales Lead.
Find someone that is more technical than most salespeople. It could be someone in pre-sales or even a former CTO who understands the product and how it works, in addition to understanding your customers. Maybe this person will partner a more outgoing Founder for client presentations.
4. Go for an experienced Software Consultant.
Consider onboarding a consultant who has worked in one of the consulting firms that has been selling AI services for the last 2 years. There’s high-calibre talent looking to leave the consulting world for a high-growth tech scaleup right now.
5. Ask the right questions for hiring Sales Leaders - like Ben Horowitz.
In Ben Horowitz’s brilliant book ‘The Hard Thing about Hard Things’ he talks about asking the right questions in the interview process to screen effectively for those high-performing sales leaders.
Feel free to DM me and I can send over 10 killer interview questions from the famous book.
Looking to hire hungry sales leaders for your AI product?
DM me for more information and a confidential chat.