How Jeremey Donovan Sells: To Close a Deal Today, Be Ready to Speak to the How

You look at the list of roles Jeremey Donovan had in his career, and it’s easier to tick off what he hasn’t done in the world of sales and marketing.

The list of jobs he’s held includes…

• SVP of Revenue Strategy for SalesLoft,
• Group Vice President of Marketing for Gartner,
• Chief Marketing Officer and SVP of Sales for the American Management Association,
• SVP and Head of Sales Strategy for Gerson Lehrman Group,
• Head of Sales Strategy & Enablement for CB Insights,

and now, EVP of Revenue Operations and Strategy for Insight Partners.

What has he learned in his career? What key sales mistakes does he see organizations making today? How will AI transform things?

Also, for the most ambitious of you, Jeremey’s current job includes helping companies hire their CRO. So, what does he look for when recruiting a CRO?

We asked him all of that and more in our latest edition of How I Sell:

1. What drives you?

When I take those personal personality assessments, the number-one thing that pops out is learning. And I can definitely confirm that’s the case.

One of my mantras throughout my career is to 10x out-learn people and 10x out-work people. And the learn piece is critical.

I’ve had the good fortune to switch what I do for work every few years. I was originally an engineer, moved into product development, then product management, then marketing, then sales and marketing, and ultimately revenue operations. Along the way, to make those shifts, learning was absolutely critical.

And the learning spans more than just the professional world. I also try to cultivate a variety of intellectual and non-intellectual hobbies.

So, the mantra “always be learning” drives me.

2. What's the biggest mistake you see sales teams making today? What should they do instead?

On the sales-led side, I think the mistake has to do with the following:

There are three different categories of contacts to engage. The first is inbound leads, which are true hand-raisers who are making a demo request or are asking to talk to a salesperson.

The next is intent-driven inbound or what many call ‘warm outbound.’ This is where you have first or third-party intent signals. First-party would be somebody attends a webinar, downloads content, drops by your booth, visits your website, etc. Third-party is when people show intent by researching your company, your competitors, or you category on the wider Internet.

Those two are generally fine, if they are treated separately. Because a true inbound lead needs to be handled differently than an “intent-driven inbound” lead.

The third category is where the mistake lives, which is often referred to as “cold outbound.” This is where you have an account list, and you’re trying to engage these people with a multi-touch cadence.

If your average-selling-price (ASP) is above $50,000 in annual recurring revenue, then it can make sense – given the amount of activity that prospectors can complete – to use this strategy to generate new opportunities. But, if your ASP is under $50,000 in annual recurring revenue, then it’s very likely that this will never be an efficient sales motion.

So, instead, cultivate prospects through marketing or through partners. But just going straight after them with your sales team is quite inefficient and therefore what I see as the biggest mistake sellers are making right now.

3. Buying committees are getting larger — and more cautious. What's the key to overcoming that?

Yes, there has been research out there for many years from many folks, Gartner included, around buying committees getting larger.

I believe this is an effect of a tighter economic environment. An environment where people have loaded up on the things they’ve purchased and are trying to get more efficient in general.

Plus, you often have a separation between the person who’s a signatory – which is often the CFO – and everybody else. It’s here that’s the key.

When you talk about overcoming that, I recently read a great book called The Jolt Effect. And the key takeaway from that book is that you need to approach the buying cycle in stages – the early-mid stage and the mid-late stage.

In the early-mid stage, you are focusing way more on value creation and helping the prospect see the ROI of moving off the status quo.

But what I thought The Jolt Effect did a great job of was saying there is this other thing going on. And it exists early, but it becomes increasingly critical as the deal progresses to mid -late stage, which is reducing the perceived risk of purchasing. So, for every one of those people who are on the buying committee, you need to understand and address what they are worried about.

For instance, your champion’s job is on the line if you're not successful with your implementation. And it’s not “satisfaction guaranteed or your money back”, which really doesn't exist in B2B sales. This is more about proving, through discipline and rigor, that you are going to help them realize the value that they're expecting.

And the way you reduce perceived risk is to double-click into the ‘how.’ Meaning, introduce abundant—almost borderline excessive—detail around your implementation processes and case studies around implementations that went well.

Even talk about the implementations that didn't go well. Because, if you communicate that you know how to recover from the ones that hit bumps, I think that gives people a lot of emotional safety.

The second thing we are seeing is executive relationships have become more and more important in the buying process. The key here is getting your execs matched up with their execs early in the sales process.

Here’s how this pertains to risk reduction: Sophisticated buyers know that things will go wrong along the way to achieving value. What you want them to know is that when you hit a snag, large or small, someone's got their back. That they can call an executive on their cell phone 24/7/365 to get the problem escalated and resolved.

Exec-to-exec relationships will help to overcome these large, cautious buying committees.

4. What role do you see AI playing in sales moving forward?

I think of myself as more as 80% curator and 20% creator. Here I'm really going to curate an answer.

I think where the zeitgeist has moved here is a recognition that AI, at the current time, is incredibly valuable in helping with the non-human facing aspects of sales. So, what does that mean?

On the predictive side of AI, it means helping with account scoring and lead scoring. Down funnel into opportunity management, it means helping identify which factors are critical to winning deals and guiding Account Executives to focus on those factors. And it continues into post-sale as well by helping to surface customers that are most at-risk and then serving up specific plays most correlated with renewal and expansion.

There are more use cases on the predictive AI side, but those are the big ones.

For Generative AI, let’s take prospecting. In addition to the things I mentioned, GAI can help on account research, prospect research, and drafting initial messaging that should be reviewed by the seller before sending out. And that can again apply both pre-sale and post-sale.

But, for the most part, I think folks are centering now on the fact that humans still need to be involved in the actual interaction. I've seen a lot of examples lately of people testing pure AI prospecting tools and getting very, very low if not zero yield. Voice conversations with AIs are currently awkward and I’m not ready to buy from one.

We're still in the human-centric selling world. Wind the clock forward five years and it's anybody's guess. I personally have a hard time with the idea that I might purchase a B2B software product for hundreds of thousands of dollars by just interacting with an AI who is 1,000x or more smarter than me. But never say never.

5. What do you look for when interviewing someone for a CRO role?

I have the lucky responsibility here at Insight Partners to interview quite a number of people for CRO roles. And there are several things we look for.

One of them that I think is an absolute-must is they need to have been through the particular scaleup journey that we're looking for. So, for instance, if a company is going from $10 million to $100 million or $50 million to $200 million, it’s absolutely critical that they have experience leading through the same growth.

Also, we're looking for people who have managed teams with a very similar sales motion to the motion that the company is trying to execute. So, for instance, if a company’s normal ASP is $100,00 to $250,000, with a nine-month enterprise sales cycle, you’re looking for someone who is a close match to that.

The third piece we’re looking for is their ability to identify, recruit, coach, and manage talented individuals. I really want to understand that they have a systematic approach to how they evaluate talent. There are different approaches; one of my favorites is I-C-C-E, which is Intelligence, Coachability, Character, and Experience. It's just one of many frameworks, but that one makes a lot of sense to me.

Another thing we look for when we're hiring people is a disciplined operating rhythm. I read a post recently that mentioned you really want somebody who comes in with a playbook written in pencil, rather than pen. I thought that was really smart, so I'm looking for that playbook, that operating rhythm, of what they plan to do with their team. Week in, week out, across every week of the quarter, and every quarter of the year, what meetings, what's discussed, how, in what detail.

And last is their interpersonal working style and the company’s style. For example, some companies have a more direct, confrontational working styles, whereas others are more indirect. So, matching with the culture of the company is really important.

6. What's the best piece of sales advice you ever received? 

I'll tell you a story that I’ll always remember.

One of the CEOs I worked for was once asked, “What’s the best cold call you ever got?” And he described a seller who reached out and was able to connect with him.

Here’s what happened – the seller give his elevator pitch and asked if the CEO was interested in continuing the conversation. Our CEO said he wasn’t. But the salesperson responded, “Are you sure you want to do that? Are you sure that you’re truly not interested in learning more?”

Our CEO said “okay” and wound-up hearing more.

The point is that sales success goes to the bold and the brave.

So often I get cold calls and I’ll say I’m not interested, and the person will just hang up. You could argue that if a person says they're not interested then they’re legit not interested, don't waste any more time, but I think it's worth understanding why they are they not interested and have the bravery to power through at least one initial objection.

Another great piece of sales advice is there are no silver bullets. It’s all about activity and effectiveness.

Activity is showing up, and effectiveness is showing up better. The first is about effort and the second is about learning.

To get more effective, you need to seek feedback. Read. Ask your manager to review your sales calls. Ask sales enablement to review them too. And keep practicing.

If you continually practice in a feedback-rich environment, you’ll drastically improve. But many teams aren’t generous with their feedback so be proactive and ask for it. That’ll greatly improve your skills over time.

7. Is there any habit you have outside of work that you believe helps you perform better? 

I’ve got two, a habit and an anti-habit.

One is I’m a voracious reader and I try to read fairly broadly. I break my reading down into fiction and non-fiction. These days, I read a lot more fiction and my go-to genres are literary fiction and sci-fi.

Fiction gives you a perspective on the world and on how people think and behave. And sci-fi helps you think about the future and the potential implications of new developments.

On the non-fiction side, I devour sales and customer success-related books. Of course, I read about other functions when I was in those jobs. For example, when I was in marketing, I read a ton of marketing books. And I also read many business biographies.

All of that helps me perform better at my current job because it speeds up my rate of learning.

The anti-habit is I don’t watch television. Everyone needs to find a way to relax, but TV doesn’t relax me. And the side benefit of that is it provides me productive time for personal and professional endeavors.

8. What was your biggest failure in sales and how did that experience transform you?

I had this very long belief that you can play a sort of “Moneyball” of hiring sales talent.

I’ve charged at the windmill a few times where I’ll take every salesperson who ever worked for a company and bio-profile them. Where did they go to school, what was their degree, how long did they work in sales before they came into the role, did they work in the vertical market before they got hired, did they work in the horizontal market, do they list President’s Club on their profile? Everything you can pull about an individual from the public domain.

Using that I try to find correlations with success. Since I don’t have performance-to-quota, my proxy for success is lasting in the role for at least two years.

I have found correlations between different biographical factors and the ability to last 2+ years in a sales role. Yet, I haven’t been able to get other people excited about it.

I need to spend more time on why people don’t see value in this approach. Perhaps there is something fundamentally wrong with my approach or maybe it’s more behavioral resistance.

So, I consider it a failure because I’ve had this theory for so long and now data to support it, and yet haven’t been able to have an impact on how people hire. I want people to hire people who are going to last at least two years, because I don’t want people to get hired and not make it when they could’ve made it somewhere else. And it’s obviously very disruptive to companies to hire the wrong people and experience high turnover.

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Recent editions include:

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