I meet a lot of B2B tech founders who are frustrated. They’re doing the discovery calls, having great conversations, building rapport, and then it all goes quiet after they send the proposal.
Sound familiar?
This is happening because you’re treating proposals like a checkbox on your to-do list rather than the strategic selling tool they actually are. You’re doing light discovery, then slapping a proposal on someone’s desk (or in their inbox), and wondering why they’re ghosting you.
I’ve seen this pattern dozens of times. The founder has three or four meetings in a day, feels productive sending proposals out quickly, and then… crickets. The win rate sits at 8-10%, and everyone blames the market or bad leads.
But it’s not the market. It’s your approach.
The two fatal flaws
1. You’re not doing enough discovery
You’re not finding the real cost of the problem. You’re scratching the surface, getting some pain points, maybe a few feature requests, and calling it done. But you haven’t dug deep enough to understand what this problem is costing them in revenue, in time, in people leaving, in competitive advantage lost.
Download our guide on how to nail your discovery process here.
2. You’re sending proposals to the wrong person
Someone opens your proposal, sees it’s going to cost £30k a year, realises they don’t have budget authority, and ignores it. You’ve just wasted all that discovery work by putting your proposal in front of someone who can’t sign the contract.
Why your proposals feel like costs, not investments
Most proposals speak the company’s language: I see it all the time. We help companies increase efficiency by 40%, or Our platform saves teams 10 hours per week, and Industry-leading ROI.
That’s all fine, but it’s generic. It doesn’t speak to what Sarah the VP of Sales told you in discovery, that her team is missing quota three quarters in a row, that her best AE just quit because the CRM is a nightmare, that the CEO is breathing down her neck about pipeline visibility.
When your proposal speaks your language instead of theirs, it becomes another cost to evaluate. When it uses the exact words they used to describe their pain it becomes the solution to a problem they’re desperate to solve.
The three-step framework
I’ve used this with founders who’ve gone from 8% win rates to 33% in under a year.
Step 1: Do real discovery and find maximum pain
Discovery isn’t a 30-minute call where you demo your product and ask what their biggest challenges are.
Real discovery means:
- Understanding the full scope of the problem and its downstream effects
- Calculating the actual cost of inaction (lost revenue, wasted time, turnover, missed opportunities)
- Identifying everyone involved in the buying decision
- Learning what each stakeholder cares about
Ask yourself whether you could walk away from the discovery call and build a credible business case for them, even without your solution. If you can’t, you haven’t discovered enough.
Step 2: Co-create a business case in their words
Now here’s where most founders go wrong. They take all that discovery work and translate it back into their company’s marketing speak.
Don’t do that.
Your proposal should read like a mirror of what they told you. If they said their current process is burning 15 hours a week per salesperson, that exact phrase should be in your proposal. If they said they’re losing deals because they can’t respond fast enough, use those words.
This does two things:
- It proves you listened and understood their business
- It triggers the memory of that moment of maximum pain when they were most vulnerable
When you put the price on the table after reminding them of all that pain, it becomes a no-brainer. It’s not an additional cost, it’s the cost of solving a problem that’s already costing them far more.
Step 3: Present it live, don’t email it
Never, and I mean never, just email a proposal and hope for the best.
Book a meeting to walk through the proposal. Here’s why this is non-negotiable:
- If they told you in discovery that their CFO and VP of Sales both need to approve, you can invite both to the proposal review
- You can read the room and see where they flinch. What gets them excited? What concerns do they have?
- You can adjust in real-time based on their reactions
- You eliminate the risk of the proposal sitting unopened in someone’s inbox while you anxiously wait
I’ve seen deals saved because the founder noticed a concern on someone’s face during the proposal walkthrough and addressed it immediately. You can’t do that over email.
A real example: From 8% to 33% win rate
Two and a half years ago, I worked with two founders selling a martech product at £30-40k ACV. They were seeing an 8% win rate.
The problem? They were having meetings with marketing managers, doing light discovery, then quickly firing off proposals to hit their daily quota of outreach. They thought speed was efficiency.
But CMOs were the ones who signed contracts. So, they were putting proposals in front of people who couldn’t buy, with incomplete information, using language that didn’t resonate.
Here’s what we fixed:
- Entry and exit criteria for pipeline stages: Before entering the proposal stage, they had to have specific information including who the economic buyer was, what the cost of inaction was, and what success looked like in the prospect’s own words
- Weekly pipeline reviews: They started asking themselves “Have we actually earned the right to send a proposal to this opportunity?”
- Better discovery frameworks: We trained them on how to find the real pain and calculate credible ROI
Within six to nine months, their win rate jumped to 33%. Today, that company is over £5M ARR with a full sales team. They successfully transitioned from founder-led sales because they built a repeatable, scalable process.
Your Action Plan
Here’s a framework I recommend to every founder. Create a win plan for each major opportunity.
A win plan is simply a document that answers:
- What’s the clearly defined problem (in their words)?
- What’s the cost of inaction? (Lost revenue? Employee turnover? Competitive disadvantage?)
- What’s the credible ROI calculation? (What happens if they do nothing vs. what our solution costs)
- Who needs to sign off, and what does each stakeholder care about?
- What actions do we need to take to win this account?
When you have a win plan, it becomes obvious what’s missing. If they mentioned another stakeholder needs to be involved, you know you need to get them in the room. If they said their current process costs them £200k per year in wasted time, that number needs to be front and centre in your proposal.
It keeps you focused on what matters. And that’s solving their problem in a way that makes economic sense to them.
A disciplined approach
Co-creating business cases isn’t complicated, but it does require discipline. You need to:
- Do real discovery – Find the maximum pain and the cost of the problem
- Speak their language – Use their words to describe their problem and your solution
- Present live – Walk through proposals together with all decision-makers in the room
- Build win plans – Know exactly what you need to do to earn the business
Stop treating proposals like a task to tick off your list. Start treating them like the culmination of a strategic selling process where you’ve partnered with your prospect to build a case for change.
That’s when you stop hoping deals close and start knowing they will.
Author Bio: Matthew Codd
Matthew has 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.
He now uses his experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.
Matthew co-founded Cosmic Partners in 2022, a SaaS sales recruitment specialists for VC backed B2B tech companies.
