What We Learned on the Sales Hacker Roadshow (2022)

If you joined the Sales Hacker community in the last four years, this might be news to you: Sales Hacker was originally known mostly for its incredible in-person events.

But (and it’s painful to admit this) until this spring, we hadn’t hosted a physical event in nearly four years!

We’ve been focused on other things. To name a few:

But we found that as this glorious community grew in size, we weren’t proportionally growing the sense of community we feel with our members and that our members feel with their peers.

And we decided we needed to improve that. Enter: the Sales Hacker Roadshow ‘22.

What Was the Sales Hacker Roadshow ‘22?

In the last week of April and the second week of May, we hosted five afterwork events in five cities: Boston, New York, San Francisco, London and Chicago.

We gathered together small groups of our members for rousing discussions, sharing ideas, networking, and some food and drink.

We met incredible attendees from companies like Twilio, Wells Fargo, Lattice, Education First, LinkedIn, Salesforce, Accenture, and Uber.

Rather than packing the evening with sessions, we shared some data from research done by Outreach and Forrester and most of the night was then spent discussing the data and networking.

The topic? What does it take to be a top rep or leader today, and how is that different from ten or twenty years ago?

Want to know exactly what we shared, and what community members added to the conversation? Keep reading.

What We Shared (And What We Learned)

To set the stage, I can’t emphasize enough that we designed these events to reflect what it means to be a Sales Hacker.

You may steal best practices from others, but you don’t rely on them. You make intelligent, intentional decisions to continuously push for revenue growth using the data and the tools you have available to you.

And among those tools, your own critical thinking is your best.

So while you’ll see some data here, and some insights from myself and those who attended the events, keep in mind that you’re the best judge of what will work best for you.


Sales Hacker Roadshow - Revenue Leaders Deal with Myriad of Challenges - image

Much of this data is from a Forrester Consulting study commissioned by Outreach in 2021, and collected data and feedback from 212 sales leaders in North America and the UK. So keep in mind: these responses came amidst the most rapid (and frankly scary) change any of us have ever seen in sales.

So imagine my surprise when these 212 sales leaders said their biggest challenge that year was managing a multi-generational sales force!

A show of hands at each event showed me I wasn’t alone in being surprised. I think only one person in NYC said they weren’t surprised.

I’d have certainly thought that the economic environment or the pace of change would have been greater challenges.

But then the more I thought about it, the more this made sense: these sales leaders are taking note that the environment their sellers face is entirely different from the one they faced when they themselves carried a bag. So they’re not exactly well-equipped to tactically guide their sellers through the selling environment.

How exactly is the selling environment different than it used to be?


Sales Hacker Roadshow - Changing Dynamics Create New Challenges for the Sellers - image

One thing that’s different about sellers today is that they themselves are dealing with a generational change. Many of them have been taught to sell by people who haven’t ever sold to Millennials. And yet this data from LinkedIn showed that 48% of Millennials say they make B2B buying decisions.

Related: Don’t Call, Just Text: How to Sell to Millennial Buyers

And a different Forrester study showed that between 2019 and 2020, the average number of touches it takes to close a B2B deal increased by 58% – from just 17 touches in 2019 to 27 touches in 2020. So sellers have to sell to a different kind of person, and they are managing much longer and more complex sales processes.

Not to mention the fact that a Gartner study also found that the average number of stakeholders in a buying committee is 11 – a number can that can flex up to over 20. So we’ve seen it said before: the single individual as “decision-maker” no longer exists as it used to either.

Those are three significant changes. No wonder leaders aren’t quite sure how to manage their younger sellers!

Though I will say – I personally think they mis-named the problem. The challenge they face isn’t the generational gap, it’s the fact that the selling environment is different today.


Sales Hacker Roadshow - Tech and Digital Savvy Modern Sales Reps - image

What does this mean for the skills and behaviors it takes to be a top-performing rep these days as opposed to what it meant to be a top seller years ago?

Back to that Forrester report Outreach commissioned: we asked our sales leaders what they thought the most valuable attributes were in a sales rep.

Again, I was surprised relationship-building wasn’t at the top of the list here. These sales leaders were most likely to say they need their reps to be digitally savvy and technologically adept.

Some other things here that are not surprising at all: leaders do still want their reps to build relationships effectively. They want them to have industry expertise, and solve problems.

Read: Is Rapport Dead? How to Demonstrate Value in the Age of Remote Buying

But I think had we asked this question even just 10 years ago, we never would have seen ”digitally savvy” anywhere in the top 10 skills. That’s a monumental shift in what it means to sell.


Sales Hacker Roadshow - Modern Sales Rep Must Deliver More Value - image

We dug in deeper here.

We asked those sales leaders to rate the importance of various selling skills in the modern selling environment (again, as a reminder, this was in 2021).

So it’s pleasing to see that here, relationship-building tops the list. And we see leaders placing value on collaboration and managing cost of ownership conversations – classic sales skills.

Read: Top 30+ Sales Skills You Need to Become a Great Sales Rep

But again, we see some things here that I don’t think we would have seen just a few years ago.

We’re asking our reps to transform data into insights, infuse prospect conversations with those insights, and do it all in a hybrid environment, across more channels. That data stuff – that is something that used to be somebody else’s job. Marketing or an maybe an analyst would provide the insights, and the seller didn’t necessarily need to have full grasp (although it helped).

What this all means is that the job title of “salesperson” might still be the same, and the goal of the role is certainly the same, but how the job is done has changed drastically.


Sales Hacker Roadshow - Revenue Innovator Rep - image

Mary Shea, Outreach’s Global Innovation Evangelist, came up with this stripped down model of the 6 must-have characteristics of a modern, top-performing rep.

She calls them a Revenue Innovator Rep – because their job is not just to follow a process, but to innovate and act as a change agent within the scope of their influence on the sales process.

And among the six characteristics, she lists their ability to produce predictably: not just hit a number, but do it consistently and be able to prove that they will do it. Leaders also want their reps taking a digital-first approach, using platforms and tools to increase reach and engagement with deals they’re working, to organize and collaborate with that larger buying committee across more deal steps.

She points out they need a data-driven mindset, and to embrace hybrid methods of selling, too – flexibility is needed more than ever.

And of course – relationship-building never goes away.

But what did we say before I began sharing this data?

Tonight is about you and your critical thinking. The change is far from over. In fact, you, the Sales Hackers, are the ones driving it. So none of this is the final word on what it takes to be an excellent modern sales rep.


Sales Hacker Roadshow Group Discussion - Seller Skills

This is where we put it to our groups in those five cities we visited: what skills and behaviors do reps actually need to be excellent today? And what has changed from 5 or 10 years ago?

At this point in each city, we organized into groups of 5-8, shared brief introductions, and and chose a moderator for the group. After we discussed in groups for 25 minutes or so, I asked the moderators to share out a few key insights from their group.

7 Key Lessons We Learned from Members:

  1. In every city there was a general consensus that the role of the seller has changed drastically in the last 10-20 years. Opinions differed slightly on exactly what is different, so clearly we’re all still grappling with the changes. (Have an opinion? Weigh in on the community conversation.)
  1. One clear change, though: specialization of sales roles. We now have SDRs, BDRs, MDRs, Sales Engineers, growth AEs, enterprise AEs, full cycle reps… the list goes on.
  1. “Technologically adept/digital capabilities” could mean ability to use technologies (like sales execution or CRM to sell), social selling, or the ability to understand a complex product more completely. Our attendees raised an eyebrow at these data points, and left room for interpretation.
  1. Prioritization is different than it used to be. Not only do sellers have to choose the right account to target, they have to choose the right person in the buying committee, and the right channel(s) for communicating with them. And they have to do all of it at the right time, too.
  1. Sellers still need great communication skills, and need to be able to project business acumen. Nobody sees this going away.
  1. Sample size matters! 212 responses in this data set is directionally interesting, but probably not the data we all want to base career decisions on.
  2. Is it a little ironic that Forrester, a company that typically targets audiences at less innovative companies, is the one doing this research? We also wondered what industries were represented in the 212 responses.


Sales Hacker Roadshow - Revenue Innovator Leaders Invest in Reskilling - image

After we finished our first round of discussions, we dove into some more data.

I shared this slide to illustrate the point that these leaders are investing in training and enablement at the management level as well as the rep level. So clearly the reality on the ground is changing for reps, but there are skill gaps that need to be addressed in management and leadership too.


Sales Hacker Roadshow - Role of the Sales Managers - image

So we asked our group of sales leaders what skills and attributes they want their managers to have.

Almost all of us were surprised to see that “developing reps” is not at the very top of this list. Or at least in the top 5, along with coaching skills.

Read: Coach Your Way to Sales Management Success: Best Practices from the Field

Instead, we see this theme of data-driven insights and analysis again. But we also see that leaders want their managers to be empathetic. That’s different from 10 years ago, too, I think. At least, my first sales manager didn’t strike me as particularly empathetic.

Interestingly, we’re also asking our sales managers to be good at driving change. When I first became a sales manager, I was – explicitly or implicitly – told that my job was to get reps to conform to a static process. So that bit of data and my anecdotes are at odds here again – but I suspect many other sales managers have had similar experiences.

Some things aren’t different, though. Leaders still want their frontline managers to be strong coaches with experience being a top-seller.


Sales Hacker Roadshow - Many Managers Haven't Mastered Necessary Skills - image

Again, we dug in a little deeper and asked our leaders to tell us if they thought their managers exhibited these skills, or if they needed a little more coaching.

I expected to see a little more of a mix here, but many of the skills we saw on the previous slide are listed as “not achieved” for a significant percentage of their teams.

This question also showed us a few more skills that sales leaders prize: the ability to build a diverse team, to strategize on deals and hold effective pipeline reviews.

Read: Why Increasing Your Sales Team’s Diversity Improves Your Bottom Line

And again, that data and insights point: more than half of sales leaders say their managers haven’t achieved that skill.


Sales Hacker Roadshow - Revenue Innovator Manager - image

So we already talked about the new skills and behaviors a rep needs to perform at their best.

Mary Shea also proposed a similar model for the manager.

Her research showed a continued emphasis on predictability, using hybrid methods to communicate, and data. But we also see here that theme of being a change agent, and championing mental health.

Read: The Greatest Competitive Advantage You’ll Ever Know: Mental Health

Anybody think you’d have seen those last two on the same survey 10 years ago? Nope. Our attendees on the roadshow didn’t think so either.


Sales Hacker Roadshow Group Discussion - Managers and Leaders helping sellers thrive - image

We know that managers and leaders are only trying to help their teams adapt to the new selling reality on the ground. Since their reps need some new skills and behaviors to excel, it only stands to reason that managers and leaders also need to change their approach.

It’s our responsibility to build an environment where today’s top-performing reps can thrive, so they can surpass quota, stay with our organizations, and grow into our next generations of leaders.

What do managers and leaders need to do to make that happen? Make sure you don’t just focus on good principles of people management, but also the processes and tools you equip your teams with.

4 More Key Lessons We Learned from Members:

  1. Here’s an irony: especially in smaller companies, where change is the only constant, change management as a practice is not talked about or really even thought about. The idea that this is a necessary skill for effective revenue leadership rung true, but nearly every attendee acknowledged they’d need to brush up on it.
  1. Most leaders are still thinking like coaches, by their own admission. They were apt to talk primarily about good principles of people management during this set of discussions. When it was pointed out that tooling and processes were also a crucial piece of the environment they provide sellers,
  1. Excellent sales leaders listen. I sat at one table with two VPs, one CRO, a Founder and an SMB AE. Those leaders peppered the AE with all kinds of great questions about her experience as a seller for the better part of 30 minutes.
  1. Data is still an afterthought. When our attendees began to talk about how they could support sellers, they shared a ton of great ideas. But most were not based on data-driven insights about what is provable to have an impact on positive revenue growth. Things like more transparent comp plans, more consistent coaching, calmer pipeline reviews are all great ideas. But they’re also table stakes in the new buying environment. Leaders are still working on gathering the data they need and putting in a form that actually helps them make better decisions.

What’s next

Don’t let the conversation end. Jump into the Sales Hacker community and hear what other sales leaders are saying.

Colin is the Director of Marketing at Sales Hacker. Before that, he led the strategy team at a marketing agency, and worked with hundreds of B2B brands to build winning inbound strategies. Outside of work, Colin is the world’s biggest dog lover, and spends as much time as possible outside.

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