Human-Centered Digital Transformation for Your Sales Team

Make your digital sales transformation part of a strategy to make closing deals a simple, pleasant, and efficient process for your team.

It’s tempting to throw technology at what are, fundamentally, human problems.

For instance, you don’t like working out. So you get a Fitbit, hoping it will shame you into getting off of your b*tt. Or you get a Peloton, convinced it will bicycle for you while you watch engaging videos of forests in Norway.

We all know better, but we still hope that the next technology will solve every problem, from our dislike of running to our mothers-in-law.

Sales leaders, though we love them, are often no different. They look at a problem like teams missing quota, and they say, “there’s gotta be a tool for that.”

There usually is, and those tools are excellent. (We’re huge believers in sales execution platforms).

But, your new tools will never actually solve any problems if you focus on those tools in isolation from the people who use them. Just like a Peloton collecting dust won’t help you get ready for that itsy-bitsy, teeny-weeny yellow polka-dot bikini.

Dog in a bikini

In other words, if you’re a sales leader looking to solve pressing problems on your team, the answer is probably the right technology. However, if you want your investments to pay off, and your team to feel valued, then you need your digital transformation to be as human-(or doggo-) centered as possible.

So, what’s your problem?

There are a lot of problems you could focus on solving, but which are the most pressing?

In case you’re curious to know what dragons others are trying to slay this year, Gartner’s 2022 Strategic Roadmap for B2B Digital Selling asked CHROs to weigh in on the top challenges their organizations are facing, when planning for the future of work.

The top four are a shortage of talent, the demand for the hybrid work model, new go-to-market strategies or service models, and increased digitalization. 

While none of these are unique to sales, these problems are hitting a lot of sales departments pretty hard. They can’t get or retain reps, and the ones they have are working from all over the place and often doing their own thing, with little accountability. This makes training, onboarding, consistency, and visibility really tough.

And increases in digitalization are, across the board, shifting the way companies approach their go-to-market strategies. Naturally, this impacts sales and the way they interact with every other demand-generating department.

When you put those challenges all together, most modern sales team put these problems near the top of the list:

  • It’s tough to find, train, and keep good talent.
  • Once we have good talent, we have no idea what they’re actually doing. All we know is whether or not they’re hitting the revenue target.
  • Marketing is adapting their strategy, and they want us to come along, but we’re getting lost in the shuffle.
  • We have no idea what leading companies are doing to stay ahead of a constantly evolving marketplace.
  • In a climate of frequent change, we’re having a lot of trouble reliably forecasting revenue growth. It’s just too unpredictable. 

A well-utilized sales execution platform (SEP) can address every one of these problems, serving as the centerpiece of a sales digital transformation. But, in order to do it right, you’ve got to start with your end users.

Your digital sales transformation starts with maximizing your sales execution platform

We have written a lot about sales execution platforms and how they can help your team. However, an SEP will not, on its own, solve any of the problems above.

Instead, you need a sales execution program, which maximizes the tool’s potential and your team’s success. That includes properly supporting your sales team with strong, sales-focused messaging, clearly assigning roles and responsibilities, creating a cold calling program that makes it less sucky to spend time dialing, and offering enablement services that empower each user to embrace the platform and strategy.

Then that program needs to “plug in” to the rest of your tech stack. For instance, if your SEP isn’t talking to your CRM, then you need to pause right now and make that integration happen. And if you’re using a marketing automation platform (no, that’s not the same thing as an SEP), then you need to integrate that as well. 

For instance, many teams connect their marketing and sales automation tools to their CRM, which serves as the information hub. Then, when a lead comes from marketing, it goes through the CRM and right into the SEP, where salespeople can engage that lead. If those systems aren’t connected, then your customer journey will be bumpy and slow. Not to mention, sales and marketing will get into avoidable tiffs about dropped MQLs and inconsistent customer-facing language and promises.

This might sound like a lot, but it’s sort of like getting a puppy. If you train it well in the beginning, it won’t pee in your house for the next six years. If you think it will train itself, you’ll be puddle-dodging for all of time.

So if you put in the hard work to build this infrastructure, then your sales execution program will solve problems like the ones we just discussed. For instance, you’ll see outcomes like:

  • Greater visibility in rep’s workflows and which sales plays are converting.
  • Opportunities to “scale” your best rep, identifying what makes your top sellers successful and sharing those insights with the rest of the team.
  • Efficiency through automation, freeing reps up to spend all of their time on sales-generating activities.
  • Alignment between sales and marketing, producing a consistent narrative for customers.
  • Higher adoption of not only the platform but also of the individual sales plays within it.
  • Faster rep onboarding and increased confidence for existing reps.
  • Quick responses to inbound leads.
  • Increased volume of outbound prospecting.
  • More predictable revenue growth.

But, we’ve got news. The key to building a sales execution program that “sticks” is to include your people in every step of this process, bringing in technology to empower, not replace, the human beings who sell your product and keep the lights on.

Start every project with rep-focused discovery

Our consultants begin every project with rep-focused discovery; it’s a non-negotiable for us.

This seems like a nice hill to die on

This usually involves speaking with stakeholders and asking them to nominate a team leader or manager to serve as a liaison, and then that individual recruits a few reps to represent their peers.

It’s important, when selecting those reps, to focus on a few key criteria. If you pick the absolute best rep, but their workflow is not easily replicable or sustainable, then your team will immediately give up. So, you’ll be the most successful if you focus on reps who are:

  • Above average performers who consistently hit quota.
  • Balanced people. They should “have lives” and not work 60 hour weeks. (In other words, pick a bar that won’t burn out your team).
  • Invested in others on the team. They can (and probably should) be competitive, but not at the cost of their willingness to put in time that will allow others to get ahead too.
  • Interested in strategy and messaging. If you pick reps who couldn’t care less about the sequences or cadences that end up in your SEP, then you’re not going to get a lot out of your conversations with them.

Once you’ve identified 2 or 3 reps, it’s time to have conversations with them about technology, messaging, and enablement. Here’s how.

Configure your technology based on how your reps will actually use it

We help a lot of teams unbox and onboard their SEPs, and that process always involves workflow interviews. If we don’t understand how reps will be using the platform, and what their design criteria are for the way it’s set up, then they’re not going to use it.

For example, we ask questions like this:

  1. What browser they use.
  2. What email server they use.
  3. Whether they handle inbound, outbound, or both.
  4. Where they get leads or prospects, and how they’re assigned.
  5. How they use their inboxes, CRMs, and other existing tools.
  6. How they schedule meetings and use their calendars.
  7. What happens to unresponsive prospects and meeting no-shows.
  8. How they prioritize and track their tasks.
  9. How they log activity.
  10. What the handoffs look like with marketing and customer success.

Because the SEP will talk to their inboxes, CRMs, and calendars, it’s vital to understand how to connect those tools and eventually train them. For instance, some teams will work mostly out of their inboxes, with SEP extensions open, offering access to shareable messaging, task management, meeting invitations, follow up sequences or cadences, and other SEP functionality. This is often most relevant for account executives and other closers.

There are other teams who will want to work mostly from their CRMs, using the same extensions. They’ll find a segment of leads or prospects in the CRM, put them directly into sequence or cadence from there, and make sure those engagements are tracked there, in the system of record.

Lastly, other teams will hang out in the SEP and do all of their engagements directly from the dashboard. This often works really well for XDR teams whose lists are uploaded and assigned to them, right in the SEP. 

The bottom line is that you should ask as many questions as possible to understand how to make technology work for your end users.

Co-create your sales messages with the “voices” who speak for your company every day

We will not do a go-to-market messaging or content project without bringing in the people who will be speaking or writing those messages every day.

Think about it. You’re quite literally putting words in their mouths. If those words don’t feel natural, then they’ll use other words and abandon the sequences or cadences you’ve invested significantly to create. And rightly so.

It only makes sense to invite input from the very people who already speak/write for your company every day (often with hundreds of people). Not only does it respect and acknowledge their expertise, but it also taps into a reservoir of first-hand knowledge you won’t get any other way.

If there are personas or industries that are really biting right now, they’ll know. If you’re crashing and burning with others, they’ll know that too. Not to mention, they will have experimented with 100 different ways to pitch your product on the phone and via email. If there’s a particular turn of phrase or cold call opening line that resonates, they’ll be the first to tell you.

(Hint: If your sales team’s culture isn’t currently open to inviting this sort of feedback from sales reps, then this article may help).

That’s why we ask reps questions like these, when creating sequences or cadences for their SEPs:

  1. In your own words, what is the product or service you’re selling?
  2. Who do you most often sell it to?
  3. What are their pain points, and how do they talk about them?
  4. What value propositions do you share, and how do you discuss them?
  5. What resources do you often share for social proof?
  6. What channels do you use to engage prospects?
  7. How much manual activity or personalized writing do you do for each type of persona you talk to?
  8. How long do you engage a prospect before giving up? What happens then?
  9. What are your primary calls to action?
  10. What are things you’ve learned NOT to say?

Once we’ve concluded the discovery process, we share drafts, invite ongoing input, and stay in frequent communication with the reps who helped to design the messaging. If they’re not satisfied, then neither are we.

You should lead with the same attitude. The truth is, your sales reps are your most valuable assets. It doesn’t matter how much money you have invested into a software product or a package of sequences or cadences.

Your people use those tools every day to connect with other real people: your very human prospects. Your job is to facilitate as natural and genuine a connection here as possible, inviting conversations to spark between someone who has a need (your customer) and someone  who can help them (your rep).

Let’s face it, human connections (and, yes, competition) are what make sales rewarding. Nobody gets jazzed about being a factory for sending out pamphlets and one-pagers. In an age when employees want more than ever to be connected to a mission, a “why” for their work, generic and product-focused messaging simply just doesn’t cut it.

When you allow your reps to be part of ideation, and the sequences and cadences they use reflect the way they naturally communicate with prospects, real conversations start. And real conversations lead to more closed deals.

Empower your enablement team to do more than build decks

Sales enablement is far more than producing decks and newsletter-style emails. True enablement is about creating a motivating team culture and empowering reps to be as successful as possible.
This starts with picking an enthusiastic person to own this initiative. If your enablement team isn’t excited about your sales strategy, then your reps won’t be either. (In other words, don’t hire the teacher from Ferris Bueller’s Day Off to lead your enablement team).


But it’s one thing to pick an enthusiastic person (or people); you also have to keep them feeling this way. This means avoiding the common temptation to treat enablement as a lesser function with few opportunities to express creativity or take ownership.

At many orgs that want to transition to RevOps, enablement is one of their first hires precisely because of the potential this department has to drive culture, create supportive materials (and sometimes even write sequences or cadences), and design processes to sustain the team’s goals. 

Even if this isn’t your enablement team’s main focus, you should award them a similar place at the table. And when you do, encourage them to be a “voice” for the rest of the sales team. If they’re proactively encouraged to create strong relationships with sales reps, and frequently ask them what they need, then your enablement team will have a strong pulse on your sales reps.

This will mean they produce more relatable training, create resources that address felt needs, release updates and communication at a pace that matches demand, and work alongside the folks who might be struggling with adoption.

You don’t have time to hold hands and walk alongside individual reps, but your enablement team probably does. Give them the opportunity to do so, and they will help keep your team moving forward.

In an enterprise org, this might look like utilizing survey programs to ask a lot of questions or creating focus groups to understand reps’ needs. In a small business or startup, this probably means diving into the weeds right next to reps. They might shadow them, interview them, or even do the XDR role a few days a week to understand what it’s actually like.

No matter what specific strategy they employ, the goal is always the same: approach your sales team with empathy, curiosity, and a desire to help. From there, it’s their job to create whatever resources (training, documentation, updates, videos, etc.) those reps need to succeed.

Don’t leave your sales team out of your change management strategy

By now, we’ve made the point that your sales reps should be very involved in driving your sales team’s strategy. This doesn’t just apply to the component parts of your sales process, it’s also a critical pillar of the overall digital transformation for your sales team.

If you get a strong sense of what your team members envision for the future, and where they want to grow as individuals, you can step back and compare that to your vision. Are there areas of overlap or conflict? Are there more conversations to be had, in order to understand what would constitute a “win win?”

Then, as you’re building out your vision and plan for digital transformation (for instance, move to RevOps within two years or implement an SEP within three months), you can tie that back to your team’s goals. How would achieving that objective move their careers forward or make it easier for them to do their jobs? 

When you sit down and lay out a plan, instead of focusing on numbers and graphs, share this with them. Have a conversation, which is not only open to their feedback but also speaks directly to what they care about.

If you approach change management this way, you’ll be far less likely to have a coup on your hands. Instead, the final strategy will have everyone’s fingerprints all over it, and they will feel a sense of ownership that leads to adoption, loyalty, and fulfillment.

(For more support here, you can check out our piece on how sales execution programs help teams transition to RevOps. It offers more context on how to overcome your team’s natural fear of change).

Don’t forget to bring your managers into the process, too.

It’s not enough to build a solid change management plan with rep involvement. You also need to bring in managers, understanding how it will impact their strategies for managing their teams.

They will have to enforce whatever changes you enact, so they need to believe in it. Involve them early and often to ensure that they’re able to back you and keep their reps’ best interests at heart.

This might mean adding a manager to the list of people you interview during discovery. Or, it might mean doing separate enablement (we strongly encourage this) with managers to teach them to use reporting dashboards to see all of the metrics on activity and performance they need to coach their reps.

Your team’s digital transformation should make it easier for managers to lead their teams. If it doesn’t feel that way to them, or you haven’t configured your tools and strategies to make that happen, then you need to work with your managers until you’ve checked that box.

We’ve seen too many instances when reps get excited about a new process or tool, and then their managers just don’t support or encourage it. What would have been high adoption and significant innovation stalls before takeoff.

If you’re really struggling here with managers who just don’t want to come along for the ride, then you can review this piece on creating alignment around RevOps. There’s a section on sales managers (and every other persona you’ll need to back you up), which offers talking points to turn the conversation around.

While we hope this is successful, we would be remiss if we didn’t warn you that there may be managers who are just not invested in your team’s digital transformation. They prefer the status quo, and they’re just not open to change.

If this happens, or you otherwise identify a toxic team culture under a manager who is not open to input and collaboration from sales reps, then it may be time to replace them. As hard as this choice might be at the moment, it can be one of the most critical steps you take to protect the vitality of your digital transformation. 

The bottom line is that your sales team transformation shouldn’t leave people behind.

Let’s camp for one more minute on the power of your team’s culture. If you invest properly here, and you bring your team along, they will embrace your sales team’s digital transformation with open arms. If not, the fear of uncertainty and unpredictability will hold everyone back

Don’t believe us? LeanData and SalesHacker looked at the top barriers preventing teams from embracing RevOps (the ultimate goal of most teams’ digital transformations), and culture is at the top of the list.

If you want to prepare your team’s culture for change and innovation, then you’ve got to prioritize your team members’ mental health, create an open channel of communication, and invite participation.

Sales doesn’t have to be a profession with high turnover and stress. It’s within your power to rewrite that narrative, starting with your team. Your digital transformation should be one part of a broader strategy to make it more simple, pleasant, and efficient for your sales team to connect with prospects and close more business. 

If your team needs support creating the sort of environment where reps and prospects feel valued, and your tools serve your people–not the other way around–then let’s talk about how we can partner with you in transforming your sales team from the inside out.

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