Improve Sales Execution ROI and Adoption at Three Market Segments

Enterprises, mid-market companies, and startups face unique challenges in maximizing sales execution ROI and adoption.


Despite your best efforts, getting your team to adopt a sales execution software may be harder than you expect.

Though well worth the lift, sales execution is often a feat of change management. Your reps may not understand the value, want to change their workflows, or believe leadership considers it a priority. 

This is true for companies of all shapes and sizes, but the strategies that successfully motivate teams to adopt sales execution are different at the three major market segments: enterprise, mid-market, and startup.

This is a crash course in driving sales execution adoption and ROI for each market segment. Leaders can lean on these insights to build their own game plans for encouraging higher adoption within their revenue organizations.

Abundance is both a strength and a weakness for enterprises making the change to sales execution.

Enterprises have enormous potential to resource their sales execution programs with the right experts to fly the ship to the moon. 

But their slow pace of change, office politics, and path dependence can halt progress before teams have had the opportunity to prove the value required to unlock those resources and win over skeptical reps.

Seasoned reps and sales executives have been doing things the same way for a while, and they likely developed their own playbooks well before sales execution technology existed.

Asking them to take on a completely new way of working, especially one that’s less manual and feels less personal (even though this is not the case), is going to be met with a lot of opposition.

This isn’t only true for front-line sales reps. Enterprise path dependence can also create tension with complementary teams (like marketing and customer success) and turn more stubborn sales managers against you.

That’s why you have to anticipate your company’s unique office politics and get the right buy-in, at the right levels, to get everyone on the same page.

If you’re trying to navigate challenges like these, then here’s how you can navigate past them and create momentum for your sales execution program.

Revenue Operations Job Description Ebook Cover

Download our RevOps Job Descriptions Guide

These job descriptions are a guide for revenue leaders to begin positioning their growing teams for revops domination.

Driving enterprise software adoption requires cross-departmental involvement, executive buy-in, and social proof.

Remember that sales execution and RevOps programs are cross-departmental efforts.

While sales can lift a lot of the burden, your sales team can’t run or improve sales execution programs alone. Even if sales writes all of the messaging for the SEP, that messaging still has to be aligned with marketing and customer success.

If it isn’t, then your customer experience and brand narratives will be disjointed. Promises made at the top of the funnel should align with sales conversations and, ultimately, the reality of your product or service.

This is why we strongly encourage teams to create a cross-departmental sales messaging program, which invites participation from marketing, customer success, and sales leadership.

Most importantly, however,  your messaging program has to involve sales reps. Your sales messages should sound like your reps actually communicate, without sacrificing your brand and overall go-to-market strategy.

To achieve this balance, you need input from many different stakeholders. The more involved they become, the more likely they will be to support your overall sales execution strategy.

Do everything you can to get a visible executive to champion your program.

Every company’s culture is different, but most managers pay attention when executive leadership weighs in. If you want your sales execution program to feel like a priority, then make it one beyond your team.

You can achieve this through many means, which should include three tiers: fellow executives, management, and end-users.

Your chief revenue officer, or the executive sponsor who has final sign-off on your SEP and related spending, is likely a part of shaping the company’s go-to-market strategy. Not every company properly factors in sales execution, when shaping their wider demand generation efforts and messages.

Your executive sponsor should champion sales execution as an important piece of the go-to-market strategy, connecting the sales and marketing hemispheres and aligning processes and messages across the entire buyer’s journey.

Additionally, we advise that executives participate in a meeting with sales managers, and they help to present the business case for a sales execution program. Additionally, they can reinforce expectations, ties to compensation, and paths to internal recognition and rewards.

Lastly, with end-users, executives can offer the sales team a shoutout through a company-wide channel, emphasizing their excitement to watch the sales execution program grow. Offering a shoutout to specific teams, managers, or even users who are hitting it out of the park, or who have been a part of an implementation, goes a long way.

Run a pilot to prove the value you’ve promised.

If your executives back your sales execution program from the top down, then the last piece is bottom-up proof of the value they’re championing. You will be the most successful if both layers of your organization are reinforcing one another.

The best way to prove value is often with a pilot program, which focuses on one team, region, or line of business. Pick it not based on the value to the company but on the team’s eagerness to participate. You will see the best results from willing participants.

Equip that specific team with as much of the messaging, technical enablement, and resources you can provide to help them be successful. Work with their managers to identify and recognize performance and signal the broader importance of their efforts. Learn as much as you can from the data and insights flowing through the SEP.

Then, when you start to see compelling results coming in, broadcast that success. Sales teams are notoriously competitive, and if there is one team that is clearly benefiting from a solution, the others will be much more motivated to want the same edge. 

The best champions for your sales execution program will be your users, sharing their experiences with others and encouraging them to jump on the bandwagon.

Sales execution software helps mid-market companies that have to scale, whether they’re ready or not.

If you’re at a mid-market company, then you likely feel the tension of moving at the speed of light while you’re also trying to innovate on, systematize, and document your processes.

To keep up with growth, you have to start pinning down and unifying what your reps are doing. But for those who have been with the company since the startup phase, increased structure and reduced independence can feel stifling.

This often leads to costly turnover, which is most damaging when the people leaving are taking critical knowledge with them. 

But this isn’t the only turbulence you’re flying through. Frequent changes in leadership, expectations, and even vision can make mid-market companies feel unstable and unpredictable.

Your primary goal here is to create a team culture that feels stable and directed, even if you’re dodging asteroids left and right.

The good news is that improving sales execution strategies can help you achieve this and other goals. Sales execution software allows for experimentation, rep-driven messaging, smart automation that allows for easier scale, and consistency in expectations.  

Here’s how to get your team on board and start achieving these benefits for your sales org.

Driving mid-market adoption requires regular audits, clear goals, and manager involvement.

Regularly audit every aspect of your sales execution program.

It won’t feel immediately productive, but you have to bite the bullet and do regular audits of your messaging quality and strategy, conversions and attribution, rep activity, technical functionality, messaging and platform adoption, and rep engagement.

This won’t be a huge lift, if you develop a good process for pulling and analyzing the data that’s in your SEP. And when you do this well, you can easily point to the areas which need your most pressing attention and which are humming on their own.

 Because you and your team are pulled in so many directions, allowing data to dictate your priorities helps to clarify the best use of resources.

Set clear short-term and long-term goals to prioritize the million things that feel urgent.

If you build a rhythm for auditing your sales execution program, and you’ve highlighted the areas that most need your attention, you can use that information to inform your team’s short-term and long-term goals to improve sales execution.

You already have KPIs in place that you’re chasing. However, big picture KPIs are only achievable if they’re broken down into specific criteria, and each of those criteria is backed by an actionable goal.

Metrics within your SEP are like mile markers on the way to those KPIs, and it’s critical to understand how to interpret those metrics and identify the strategies it takes to move the needle.

For instance, if you have a revenue KPI, then you need a specific rate of conversion from your prospecting efforts. And those conversions need to be mostly deal sizes above a certain dollar amount.

That conversion rate depends on not only reaching a high number of prospects, but it also relies upon reaching the right prospects, who are probably decision-makers. Those decision-makers need to hear from you with the right messaging and engagement types to start conversations.

But if your sequences or cadences intended for those personas have low open and reply rates, then you won’t hit the number. Or, if you have a lot of technical errors, then your reps will put people into sequence or cadence, but the prospects will never hear from you.

That’s why, following your regular audits, you should set short-term goals to address immediate problems and long-term goals to increase metrics that you know should be higher. If you don’t break down your KPIs like this, then you’ll never reach them.

Get managers involved early and often. You can’t do this without them.

Sales managers at mid-market companies may not be involved in the decision-making process to buy an SEP, but they’re technically responsible for getting reps to use the SEP, once it’s been implemented.

This can put managers in a tough spot, as executive leadership expects them to champion something they likely don’t understand. At first, an SEP might sound like more work or a request to reinvent the wheel. And, if their reps push back, they have very little motivation to spend time or special capital fighting them on it.

That’s why it’s critical to get managers involved as early as you can, ideally before you’ve even made a decision on a platform. But, if it’s too late for that, then bring them in today.

You should have an intimate understanding of the challenges their reps face, the solutions they’ve tried, the bottlenecks in their processes, the prospects they’re chasing down, the language they’re using, and the engagement types or media of outreach they’ve built into their workflows.

Your sales execution program should be built to address those challenges, maximize the strategies they’ve already used with good results, and incorporate their team’s “voice.”

That means including managers in crafting your sales messages, designing the structure of salesplays, offering regular feedback, contributing to enablement strategies, and seeing real-time insights on successes and quick wins.

Startups improve sales execution adoption by leaning into a shared sense of urgency and purpose.

Some startups are well funded from day one. Good for them, right? But what about the rest of the startups, who are duct taping everything and working from a garage?

Truthfully, no matter what your bank account says, startups are all launching without a lot of resources, firm proof of concept, or staff specialization. Most people are wearing many hats, jumping back and forth between what would be, in a larger organization, multiple roles.

This makes startup-land risky but gratifying. With a small team of contributors, each person “owns” a lot. Early team members can move quickly, make a potentially big impact, and solve a new problem every day.

For the right personality type, this is heaven on earth. For others, this sounds like… somewhere else. But no matter what your thoughts are on startup land, there are unique opportunities and challenges at this stage.

A sales execution program can maximize those opportunities and mitigate those challenges by offering just enough structure to fight back the chaos, while still allowing for a lot of creativity.

Here’s how to strike the right balance, empowering your lean, mean selling machine.

Document and train as much as you can, knowing it won’t be enough.

Sales enablement doesn’t exist for most startups. And, if it does, it’s probably one or two people who are pulled in a lot of directions.

That’s why you should anticipate the fact that your sales reps will not have an ideal amount of training. A lot of their learning will be through shadowing other reps and experimenting in the moment.

As you grow, encourage the more seasoned sales reps and managers to document what they can about what works and doesn’t work. If you’ve discovered best practices about messaging, sequences or cadences, or time use, then write that down somewhere and make it accessible, like in the beginnings of a sales messaging playbook.

Your sales team will have a huge amount of freedom, but that independence will be most beneficial within boundaries that direct your team’s creative energy toward the most beneficial ends.

This might mean tagging a few really successful sequences or cadences in your SEP so everyone knows which sales plays should be their defaults. Or, it might mean creating one approved evergreen outbound sequence or cadence, which is intended for a general audience and then giving your reps the opportunity to clone and customize that for specific personas. With a baseline to start from, the messages they create will be of higher quality.

Lean on grit and passion, when expertise and resources are lacking.

People who choose to be a part of a startup usually do so because they are passionate about its vision or have personality types that are well-suited to creative, fast-moving work environments.

In either case, they often bring a lot of passion, curiosity, and grit. When mixed with necessity, these qualities propel many startup employees to solve complex problems that may be completely unfamiliar to them. They’ll just dive in and make it happen.

That’s why you should give your sales team members as much ownership as you can, creating space for them to learn and innovate. For instance, if you have a sales rep who has demonstrated skills in writing and editing, give that person ownership over sales messaging quality.  Co-create standards, and then give them the power to teach and enforce them. 

Or, if a rep has taken time to go through training to learn the back end of your sales execution software, then give them responsibilities in technical administration. You probably don’t have the budget to hire someone to do this full-time, so a rep can own this function (or designate this as a portion of their role) to make sure the right settings are in place and problems can be solved in a timely manner.

While grit can’t replace an unlimited budget and a huge team, the David and Goliath paradigm rings true. Courage and a few key tools (like an SEP or, if you’re David, a slingshot) can compete with larger, slower-moving teams who aren’t anticipating a seeming underdog’s more creative tactics.

Startups ultimately drive adoption through a shared sense of urgency.

Mid-market and enterprise teams usually face more barriers to SEP adoption than startups. Because they’re small teams with limited resources, startups probably wouldn’t buy an SEP unless they were convinced it would be really beneficial.

And because startup sales teams are smaller, it’s much easier for one champion to convince all of the others to jump on the bandwagon. The combination of competition and collaboration will generally push your reps to share and take ideas.

With this in mind, the best way to get a startup team to adopt an SEP is to tap into the shared sense of urgency and show your sales team how the SEP will get everyone to the finish line faster.

If you have had early adopters using the tool consistently, and they’re seeing early results, use any means you can (like your Slack channel and team meetings) to call them out and reward them publicly. 

Explain how their persistence has not only led to their individual success but also moved the team closer to achieving your shared goals. Everyone wants to drive as fast as possible, and a well-used SEP is like rocket fuel. If you light the right fires, your team will take off.

Software adoption, like all change management, is ultimately about people. Start there.

If you’ve got a problem with platform adoption, the likely cause is not a misfiring sequence or cadence or a technical setting. It probably boils down to your people.

In order to read the full benefits of sales execution, you need your full team on board, contributing to the strategy, vision, messages, and settings. 

Without input and buy-in, no element of your sales execution program will be that great anyway. A sales execution platform, without people, is just a tool.

If your team needs further support with change management or the enablement strategy it takes to support a sustainable transition to sales execution, then reach out to our team of experts.

We’re here to take teams of all shapes and sizes from the underwhelming results that come with partial adoption to the full benefits of a thriving sales execution program.

Share with your network