“For me, it's about the humanity. We can have all this AI and all these tools in our stack, but until you can teach someone how to actually sound and act and behave like a human and bring in that humanity - that's the missing piece right now.”

Richard Harris is a veteran in the world of tech sales.  He is a mentor to many and trains sales executives through Harris Consulting Group. In this talk with Inside.com, he gives helpful advice around AI, GTM strategy, the pace at which startups should scale their sales department, and more.

Background and Sales Journey

Richard's sales journey started early, influenced by his parents' roles in sales. From his first job at The Gap to running a sales team focused on educational software, Richard's experience in sales evolved. He first noticed AI technology being used in sales about seven years ago when he witnessed the capabilities of top of funnel prospecting tools.

Evolution of AI in Sales

AI initially emerged at the prospecting level, automating messages but lacking the sophistication seen today. A/B testing has been important in refining AI generated sales messaging. Popular sales and marketing platforms with AI capabilities today include:

Wonder Way Coach
Scaling for Startups

While many founders are eager to hire sales reps or use automated AI platforms, Richard encourages founders to be their company’s initial sales rep, and show up as their human, authentic self. Startups should avoid full automation until a they have a solid understanding their ICP and the market.

When is the earliest a founder can find their first users and customers? As soon as they have an MVP. The founder should be responsible for customers 1-10, and be wary of automating too soon. Early on, founders can talk with users to find repeatable stories and use cases. When a startup scales to their first 25 customers, they should doubling down on their current verticals instead of finding new verticals. Richard advises that the best person to branching out into new verticals is not a SDR but the founder.

AI use in SMBs vs. Enterprises

Richard distinguished between small and medium-sized businesses (SMBs) and enterprises based on employee count rather than revenue. He noted that larger enterprises usually adopt AI more extensively due to their tech-savvy nature. However, the customer's comfort with AI will play a crucial role in its widespread adoption. SMB’s and mom-and-pop businesses have less use for AI right now than enterprise companies.

How sales cycles changed in 2023

“If you have a 90 day sales cycle and it's a $25 - $50k ARR deal, it's going to probably take a year to get to 25 customers. With a $10-$15k ARR, it might take six months, but in 2024, it's going to take longer.

What used to be a 30 day sales cycle is now a 90 day sales cycle. What used to be a 90 day sales cycle is now 180 days. Anything that was 180 days is 12 to 18 months.”

Sales and AI: The Future Landscape

Richard’s upcoming book, “The Seller's Journey” aims to bridge the understanding of sales as a challenging yet deeply human profession. While AI is advancing rapidly, Richard believes that customers will dictate its adoption based on their comfort with the buying experience.

Connect with Richard Harris

If you'd like to follow Richard or learn more about his book, you can connect with him on LinkedIn or visit The Seller's Journey website for pre-release and early orders before the release in February 2024.

If you’d like to get a hold of him via text at 415-596-9149, just let him know you heard him on the inside.com podcast with Stephanie, and he’ll text you back.

To stay up to date with the latest sales news, subscribe to Inside’s sales newsletter at inside.com/newsletters.

To attend Inside's next event, check out our Events Page.