Jason (Jay) Webb’s Post

My 1H of 2024 survival guide can be summed up in one word: Relationships. Thank you. Too many to tag, but you know who you are.

Catie Ivey, CRO of Walnut, recently joined me on The GOATS of Growth to discuss the differences between selling in today's environment versus selling just a few years ago. Of course, as a GTM recruiter, the thing that stuck out most to me was what she says in this clip below about the level of talent required on the go-to-market team when budgets are tight. There's a big difference between great sellers and CSMs and everyone else--and it's never been more apparent. We also talked about: -Creating buyer-centric experiences -Unit economics and KPIs she tracks -Her transition from VP to CRO -Traits she looks for when hiring -Much more Access to the full episode will be in the comments, or just search for The GOATS of Growth online or in your podcast app. Catie, thanks again for joining me! Please follow Catie for more great content.

Interview questions reveal a lot about the strength of a candidate. How much they've prepared. How much interest they have. What they value. How much they know about your business. How much they know about their business. How much they know about your competition. How they think and seek to solve problems. All reasons why a thorough interview process is important. But I'm not talking about the questions that candidates ANSWER, I'm talking about the questions candidates ASK. Intellectual curiosity has been and will remain the most desired trait when hiring salespeople. I’m no sales leader, but from what sales leaders tell me, without intellectually curiosity.. Rapid learning will suffer. Prospecting will suffer. Discovery will suffer. Demos will suffer. Objection handling will suffer. Closing will suffer. Everything will suffer. So, if you want to know how to test intellectual curiosity, especially if you're not an experienced sales leader, just use this talk track the next time you're interviewing a new sales candidate.   "We're scheduled for 30 minutes, and I'd like to use the entire time to answer any questions you have about me, the company, and (the position for which they're interviewing). Sound good?" That's it. That's all you need to say. The next 30 minutes will tell you all you need to know about their intellectual curiosity. And it will also have the added benefit of revealing other things about them like business acumen, their interest in the role, and they’re overall ability to lead a conversation.

Thanks to Gregg Carman, Founder & CEO of Chiefsight, for joining me on The GOATS of Growth podcast. Greg first appeared on my podcast 4 years ago to talk about his bias towards action as a CRO. This time around, I asked him about how Chiefsight's decision intelligence platform makes it easier for CEO's, CFO's and CRO's to take action and make better decisions faster than the competition. Listen to the mashup below for a little taste, but to learn more about Chiefsight and Greg's go-to-market strategy, please search for the The GOATS of Growth wherever you listen to podcasts, or look for the link in the comments. 

Raising money in 2024 is easy for Founders.  You just need to convey a couple of key elements in your pitch: 1. You're building a business that's worth SEVERAL billion dollars in a "base case" scenario. 2. Your value prop demonstrates that what you're offering your customers is clearly the future in terms of the value you can create for them. That's it. Easy, right? Well, easy is not exactly the way Bobby Touran, Co-Founder of Rainbow, explained it on The GOATS of Growth podcast recently, but those 2 elements, and previous relationships, played major factors in his ability to raise a $12M seed round--announced earlier this year. You'll hear him share his insights in the clip below, but to hear more about how he is building a multibillion dollar insurtech, search for the podcast on your listening apps, or click the link in the comments below. Bobby, thanks for sharing a bit of a full circle moment and allowing me to do a different kind of interview this time around. Please follow Bobby for more great content and to potentially hitch a ride on the rocket ship he has just started to fly. 

Who’s flying the plane and can they land it safely? Would you pay more for a plane ticket on a stormy day if you knew Chelsey “Sully” Sullenberger was the pilot? That’s the crux of the question everyone asks when they’re evaluating an opportunity. An opportunity to work. An opportunity to hire. An opportunity to invest. We can talk all day long about things like: Product-market-fit ICP Messaging Unit economics Process Playbooks And on and on. But in the end, it all comes down to the people. Do you have the right people on the “plane”. And, most importantly, who’s flying the plane and can they land it safely.

What's your favorite way to learn new information to stay sharp? Personally, I've never lost my child-like curiosity, so I love asking smart people lots of questions. Here's a "20 Questions" montage from the questions I've asked GTM Leaders on The GOATS of Growth this past year. What would you add?

Would you hire a recently fired VP of Sales to lead the GTM strategy for your $500K start-up, especially if that candidate had absolutely no industry experience? Likely not, right? Well, LinkSquares did. And I bet they were happy with that decision! So, what's the story? How (and why) did Steve Travaglini (Pavilion 2023 CRO of the year) get fired from one VP of Sales role, after scaling sales from $0-$7M, only to lead growth at LinkSquares from $500K to $50M in ARR over the ensuing 5 years? In the clip below he talks about what he learned in the early days of their rapid growth and what he would change going forward. You can hear the entire episode for yourself on today's episode of The GOATS of Growth podcast, but if he were one of my candidates, here is how I would summarize his attributes: --Gritty --Resilient --Adaptable --Resourceful --Optimistic --Humble And, most importantly, a STRONG bias towards action which was, in opinion, the bedrock for their strong sales culture. Steve, I had been looking forward to interviewing you for a long time and I'm happy I finally got the chance. Thanks for being such a great guest! Please follow Steve to watch as he builds his own startup, Winrate, in public. Listen to the full episode here: https://buff.ly/3Cjhr6Q

This is likely why hiring managers go silent even when you've gotten all the "buy signs" during the interview process. It's common practice for hiring managers to try to protect the ego of their top candidates. But why? Why would they want to protect the ego of their top candidates? Shouldn't that be an ego stroke, not an ego blow? Yes, but with one possible exception. What if they have another top candidate that sits on the tip top? That could be an ego blow, right? And, for better or worse, candidates' egos can get hurt when they are told they aren't wanted, or if they're not the first choice. So, the hiring manager delays, which can often manifest itself in silence. They delay because they don’t want a candidate to know that they aren’t their top choice just in case they want to come back and make them an offer. But what's happening during the silence? They're waiting just like you. They're waiting to see if their tip "top" candidate will accept their offer. But that candidate may need to delay to buy time for other potential offers they might be getting. And it starts a vicious cycle of delay for everyone. So, if you find yourself in a similar situation in the future, that may be why. I've had candidates on both sides of this equation recently. On one occasion I was representing both top candidates. A guaranteed win for me, but it's always tough conversation to have with the potential runner-up. And it's happening again. But in this case, to his credit, the hiring manager had the tough conversation directly with the candidate and has stayed engaged the entire time. (High EQ) And my candidate, to his credit, who has options and an ego, has remained graceful and patient the entire time. (High EQ) And who knows. There's still a chance the pendulum will swing back towards him. With his ego still intact.