From “One More Tool” to an Everyday Essential: Winning Proposal Software Adoption

As a strategist, staying in sync with the right communities is part of the job. Earlier this year, I paid over $1000 to join a niche operator network with curated members, promising conversations, and real potential. But there was one problem: it didn’t live where the rest of my day did. Instead of this community being housed on Slack, it ran on Circle, and despite my best intentions, I barely showed up. After a few months of lurking and guilt, I quietly cancelled.

The platform wasn’t broken, and while the content was great, I just never built the habit, and so its value disappeared fast.

The same thing happens with sales software — especially proposal software. You might be ready to bring one into your organization to speed up deal cycles, improve visibility, or tighten handoffs between teams. But will your reps actually use it? (And if they don’t, what are you really buying?)

​​And here’s a thought to sit with: sales reps spend less than 30% of their time actually selling… yet almost half of SaaS licenses go unused after 90 days. If you’ve been wondering why that disconnect exists and what it actually takes to get a sales team to embrace a new tool, you’re in the right place.

This article breaks down what we’ve learned from watching teams roll out proposal tools successfully, and what happens when they don’t. Because implementation is only half the battle, making it stick is everything!

Let’s dive in.

The sales leader’s adoption playbook

You already know proposals aren’t just a formality. They carry the weight of everything that came before: the discovery call, the solution alignment, the trust you've built over multiple conversations.

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.”

That insight is what makes proposal adoption so complex. Your reps aren’t just sending out files; they’re sending out a reflection of your positioning, your process, and their confidence in the deal. It’s not just about having a polished process — it’s your brand, your credibility, and your reputation on the line. But unless reps see the tool as making their job easier, that weight won’t land for them.

What you need from your team is to trust the tool enough to reach for it every time, not just when someone’s watching.

So how do you earn that kind of trust? Below are some tactics we’ve seen sales leaders pull to build lasting adoption. You don’t have to do all of them at once, but each one moves the needle in a real, tangible way.

Leverage peer champions to build grassroots momentum

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. Not only do they bring momentum, they also bring credibility. And when they’re the ones showing others how to get results, it cuts through hesitation faster than a top-down rollout ever could.

We’ve seen this firsthand with Qwilr customers. One of the fastest-growing ways adoption spreads is from rep to rep—just like it did at LaunchNotes.

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

As you can see, some of the best rollouts don’t start with leadership. They begin in Slack, with one rep sharing a win and others asking, “How’d you build that?” When that happens, you’re not enforcing adoption. You’re watching it spread.

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.

So when you introduce a new tool, you're not asking them to choose between good and bad, you're asking them to abandon something familiar for something unfamiliar. And unless the new option fits seamlessly into their workflow —and clearly does the job better — adoption won't stick.

That’s why integrations matter.

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.

We’re sharing this now because it shifts how you think about rollout. Adoption isn’t just about training; it’s about placement. In essence, the closer your proposal tool gets to the rep’s natural workflow, the faster it becomes second nature.

Show fast, measurable wins

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

And you aren’t alone. At Destined, a Salesforce consultancy, proposal creation used to be time-consuming and inconsistent. But after switching to Qwilr:

Once you start rolling out your proposal tool, look for ways to capture and publicise these early signals:

• Time saved on the first proposal sent
• Proposal turnaround time across the team in week one
• Templates created or reused by reps
• Customer feedback on quality or professionalism
• Faster movement from proposal sent to signed

These aren’t just internal metrics, but the kind of data points that matter to the C-suite and proof that the investment wasn’t just implemented, but is already delivering value.

Frame the tool as a competitive edge

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 you position it as a way to stand out. Interactive proposals that buyers can easily share and revisit become part of the sales experience, not just a PDF attachment at the end of the call.

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

Qwilr data backs this up. Teams using interactive features like pricing tables, view tracking, and embedded videos see higher engagement and faster closes. Buyers who spent more than four minutes on a Qwilr proposal converted at a rate of 41%, compared to just 3.5% for those who skimmed.

To help your team see this for themselves:

• Start with a polished, on-brand template they can personalise in minutes.
• Use view analytics to surface what buyers are actually engaging with.
• Share internal wins where deals moved faster or closed stronger thanks to proposal design and timing.

When reps start thinking of proposals as decision-making tools and not just documents to send, they naturally want to use what works.

Remove every possible friction point

If you're asking your team to move faster, the path from proposal to close can’t be a relay race between five different tools. And yet, that’s still the norm: build in one place, export to another, sign somewhere else, then send a payment link from another tab. 

It works until it slows the deal, frustrates the client, or gets skipped altogether. The fix isn’t just better tooling. It’s fewer tools.

When proposals are built, signed, approved, and paid — all in one flow — you reduce the number of drop-off points. And that matters more than most teams realise.

Here’s where the biggest blockers usually show up:

• Clients get stuck waiting on signatures or chasing contracts
• Reps copy-paste pricing into outdated templates or clunky PDFs
• Finance gets looped in after the proposal is sent
• Tools don’t talk to each other — so progress isn’t visible in real time

The thing is, if the workflow feels disconnected, adoption will be too. The best proposal tools don’t just help reps send faster. They make the entire close process cleaner (from quote to contract to payment) without extra tabs, approvals, or friction.

Overcoming common adoption blockers

When reps push back, it’s rarely about the tool — it’s about their fear of lost time, lost control, or another rollout that fizzles. Below is a table where we’ve broken down the most common blockers you’ll face, what’s really being said, and how to respond in a way that actually shifts behaviour.

Plus, real-world examples of how proposal tools can work with (not against) your team’s existing habits.

Making adoption stick long‑term

Now that you know how to roll out a proposal tool the right way, the next question on your mind might be “ how do I make sure this actually lasts?” It’s a fair question, considering that the early wave of excitement rarely lasts, and what you are striving for is to make the tool part of how your team sells, without pushing it every week like a gym membership no one asked for.

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

Make usage visible in pipeline reviews:

Treat proposal activity like you treat lead activity. If someone hasn’t sent a proposal, ask why. If someone closed fast with a killer proposal, dig into how.

Once proposal metrics are surfaced regularly, usage becomes a habit. (If you’re a Qwilr user, this kind of visibility is baked in with Qwilr’s analytics dashboard, which shows who viewed your proposal, for how long, and what they clicked.)

Create internal leaderboards for usage wins:

Track things like “first proposal sent,” “fastest deal closed with new template,” or “most views in a week.” These might not always tie directly to revenue, but they still matter as they give your team quick wins they can see and celebrate. That recognition builds confidence and keeps the momentum going.

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. You can even turn it into a mini competition, like best-performing slide or most creative intro gets featured.

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.

Your next move as a sales leader

If you’re leading a sales team right now, you’re likely juggling more than just revenue goals. You’re balancing rep ramp times, process consistency, and the constant challenge of making sure the tools you’ve invested in actually drive results. And it’s rarely a matter of effort; it’s that adoption takes time, reinforcement, and buy-in from all angles.

The truth is, without consistent usage, even the best sales tools can become shelfware. But when adoption clicks, when proposals become a natural part of how your team sells, you start to see shorter sales cycles, stronger close rates, and a culture that rallies around performance with clarity and confidence.

So here’s the challenge to leave with: Don’t leave adoption to chance.

Make it easy for your team to succeed by giving them the right tools, the right systems, and the right habits. And when you're ready to see how Qwilr fits into your sales stack, book a demo to see our product and integrations and see what seamless can really look like.