How to Drive Proposal Software Adoption Without Adding More Work for Reps

As a strategist, staying in sync with the right communities is part of the job.

Last year, I paid over $1,000 to join a niche operator network. Great members, valuable conversations, plenty of potential.

But it ran on Circle rather than Slack, where I already spent most of my day. So despite my best intentions, I barely showed up and eventually canceled my membership.

The same thing happens with sales software, especially proposal software. You can invest in better tools, approved templates, and a carefully designed process, but when a buyer is waiting, reps may still reach for the familiar deck or manual workaround because it feels faster.

In fact, Flowla’s 2025 Enablement Benchmark Report found that 60.9% of respondents identified low playbook adoption and inconsistent rep behavior as their biggest challenge.

So, how do you make the approved process the one reps actually use? Drawing on what we’ve learned from teams rolling out proposal software, we’ll explore how to remove friction, make the right workflow easier than the workaround, and build adoption that lasts.

Let’s dive in.

The sales leader’s adoption playbook

As sales leader Bill Kiani put it, “Proposals can make or break a deal. If sales leaders feel embarrassed, it often shows a deeper issue with alignment on value and messaging.”

For Sales Enablement leaders, there’s a lot riding on this. After all, every proposal brings together the conversations your reps have had, the value they’ve communicated, and the promises they’ve made to buyers. You want to know that all the work you’ve put into helping your reps sell better is actually showing up when it matters.

And that’s where your role goes beyond introducing a new tool. You need to help reps see its value, get comfortable using it, and eventually make it part of how they work.

So what does that look like in practice? Below are some tactics we’ve seen sales leaders use to build lasting adoption. You don’t have to do them all at once, but each one can make a real difference.

Make peer recommendations part of your rollout

Think about what you do when you’re looking for a new café or restaurant. You probably don’t Google for hours; you ask someone you trust. Sales teams are no different.

When a rep is on the fence about using a new tool, it’s not the onboarding doc that convinces them. It’s a Slack message from someone on the team saying, “This actually helped me close faster.”

That’s what makes peer champions such a powerful part of proposal tool adoption.

When reps see someone they respect getting results with a new tool, they’re far more likely to give it a go themselves. And that kind of encouragement often carries more weight than another reminder from leadership.

We’ve seen how powerful that influence can be, even before a team adopts Qwilr. At LaunchNotes, it was a proposal from another company that first caught the team’s attention.

Sometimes the proposal itself becomes the proof. As Aaron Horton, Head of Sales, puts it:

Of course, you don’t have to leave these moments to chance. Involve a few respected reps early in the rollout, let them test the workflow with real deals, and ask them what feels unnecessarily complicated. Their feedback can help you iron out the friction before introducing the process to the wider team.

And when those reps start seeing results, encourage them to share what worked. A quick walkthrough during a team meeting or an example shared in Slack can do more to build confidence than another round of training.

Integrate into the workflow, not around it

Most adoption stalls when the new tool lives outside the way your team already works.

This is where Jobs To Be Done thinking becomes useful. Every rep is already “hiring” something to create and send proposals, maybe it’s a reused PDF, a Word doc from last quarter, or a slide deck they’ve tweaked a dozen times. It may not be elegant, but it gets the job done…for them.

When you introduce new proposal software, you’re asking reps to change a routine they’ve probably followed for years. And if using the new tool means switching between systems, hunting down deal information, or starting from scratch, you can see why they’d stick with what they know.

A good place to start is where most of their work already happens: the CRM.

When proposal software shows up inside the systems reps already use, like their CRM, the friction drops dramatically. With Qwilr, reps can create proposals directly within Salesforce or HubSpot, using existing deal data. Slack notifications keep the team looped in, while everything feels native and fast, eliminating any duplicate effort.

For Enablement leaders, the takeaway is simple: before rolling out a new proposal process, look at where reps already spend their time and how they move between tools. The fewer changes you ask them to make to their existing routine, the easier it becomes to get them on board.

Show fast, measurable wins

The moment someone on your team sends a proposal in 20 minutes instead of two hours, things start to shift. Quick wins give internal champions something to share, and show skeptics what’s possible.

At Destined, a Salesforce consultancy, for example, proposal creation used to be time-consuming and inconsistent. But after switching to Qwilr:

Once you start rolling out your proposal tool, look for these early wins while keeping an eye on whether reps are actually changing how they work:

• Time saved on proposal creation
• Average proposal turnaround time before and after rollout
• Percentage of proposals created through the approved workflow
• Number of reps returning to the tool after their first proposal
• Use of approved templates and content across the team

Together, these numbers tell you two things: whether the new process is making reps’ lives easier and whether they’re choosing to use it again.

Share the results with your team, particularly when early adopters can speak to the difference in their own words. It’s also valuable evidence for leadership that the investment is delivering results beyond the initial rollout.

Show reps how the tool helps them sell better

If your proposal tool is pitched as a productivity hack, chances are your team will treat it like one: neat but optional.

The real shift happens when reps see how it can help them sell better. Interactive proposals that buyers can easily share and revisit become part of the sales conversation, giving reps more opportunities to understand buyer interest and follow up at the right time.

As Adam Taylor, founder of Media Engineered, put it:

Qwilr’s analysis of more than one million proposals offers an interesting perspective on buyer engagement. Buyers who spent more than four minutes on a Qwilr proposal had an acceptance rate of 41%, compared to just 3.5% for those who spent less than a minute viewing one.

Now, imagine showing your reps which parts of their proposals buyers are spending time on, when they’re coming back for another look, or whether other stakeholders are getting involved. That’s information they can put to use in their next follow-up, and a pretty compelling reason to keep using the tool.

To help your team see this for themselves:

• Start with a polished, on-brand template they can personalize in minutes.
• Show reps how to use proposal analytics to understand buyer engagement and plan their next conversation.
• Bring real examples into sales meetings where reps used those insights to tailor a follow-up or move a deal forward.

When reps can see how the tool helps them have better conversations with buyers, they’re more likely to make it part of how they sell.

Remove every possible friction point

Here’s a useful exercise: take a real deal and follow the steps a rep goes through to create a proposal. How much time do they spend looking for the right template, copying information, updating pricing, or checking which content they’re allowed to use?

Each step might seem small on its own, but they add up. The good news is that many of these steps can be simplified or automated. Start by looking at where reps are doing work that the system could handle for them.

For example,

• Finding the right content: Can the proposal automatically include relevant sections based on the buyer’s needs?
• Entering deal information: Can existing CRM data or meeting notes populate the proposal without manual copying?
• Getting pricing right: Can configured pricing rules guide reps without requiring them to check every detail manually?
• Preparing the final proposal: Can reps create something buyer-ready without rebuilding layouts or editing every section themselves?

This is the thinking behind Qwilr’s Smart Proposal Engine. Rather than starting with a blank document, reps answer a few questions through a guided workflow.

The engine can pull in deal information and select relevant content to assemble a personalized proposal. Enablement teams set up the process, so reps have fewer decisions to make each time they create one.

Overcoming common adoption blockers

When reps push back on a new proposal process, it’s worth understanding what’s behind their hesitation.

Some worry about losing time or flexibility, while others have been through enough abandoned rollouts to be skeptical of another one. And sometimes, they have a fair point about what’s not working.

Below are the most common blockers you’ll face, what’s really being said, and how to respond, without dismissing their concerns.

The aim is to understand where the resistance is coming from and make practical changes that give reps a reason to try the approved process.

Making adoption stick long-term

Getting reps to try a new proposal tool is one thing. Getting them to keep using it three or six months later is another. The early excitement wears off, deals get complicated, and old habits can creep back in (much like that gym membership no one asked for).

So how do you know whether adoption is sticking, and what can you do when it isn’t?

Here’s how to build that kind of staying power:

Make usage visible in pipeline reviews

Treat proposal activity like you treat lead activity.

Look at whether reps are using the approved process for eligible deals, whether they keep using it after their first few proposals, and where old templates are still making an appearance. If someone isn’t following the process, ask why. You might uncover a legitimate problem with the workflow that needs fixing.

You can also use Qwilr’s analytics to understand what happens after proposals are sent, including who viewed them, for how long, and which sections received attention. These insights give managers something concrete to discuss with reps during deal reviews.

Get frontline managers involved

Even with a simpler workflow, some reps will continue using what they know.

Managers can help by reinforcing the approved process during deal reviews, coaching reps through unusual opportunities, and following up when someone repeatedly bypasses it. It’s less about policing every proposal and more about making the new process a normal part of how the team sells.

Refresh templates every quarter

Proposals age fast. What worked six months ago might now feel off-brand or outdated. So, build a ritual around refreshing templates and pulling in rep feedback.

Feed wins back to the team

Screenshot client reactions. Share a Slack message when someone says, “this proposal blew us away.” The goal is to connect tool usage to buyer impact, not just internal efficiency. Salespeople care about results. Give them proof that the new way is working.

Aaron Horton sees this play out every day.

Bake usage into onboarding and enablement

Every new rep should send a live proposal in their first two weeks. Make it a milestone, not a footnote. When it’s embedded in the onboarding track, adoption feels natural from day one.

Give new starters a chance to work through the process with a real opportunity and make sure they know who to turn to when they need help.

Your next move as a sales leader

By now, you’ve probably realized that getting reps to adopt a new proposal process involves more than a successful rollout. You need to understand how they work, remove the steps that slow them down, and keep improving the process as their needs change.

The truth is, without consistent usage, even the best sales tools can become shelfware.

So a good place to start is with one simple question: if a rep had to send a proposal today, would they choose your approved process or find a faster way around it? Their answer might tell you more about your adoption challenges than another training session ever could.

As Aaron Horton, Head of Sales at Qwilr, explains, seeing the value firsthand can make all the difference:

So, rather than leaving adoption to chance, start by looking at where reps are getting stuck, what they’re doing instead, and which parts of the process you can make easier. The more value they see in using the approved workflow, the more likely they are to keep coming back to it.

If you’re exploring ways to simplify proposal creation, Qwilr’s Smart Proposal Engine helps reps create personalized proposals through guided workflows, connected deal information, and configured sales rules. Book a demo, and we’d be happy to show you how it works.