WonTheJob · Blog · Comparisons
Leap was one of the first digital proposal tools built for contractors. For years it was the default answer. In 2026, more contractors are switching away — and the reasons keep coming up in the same order: pricing, setup time, and no automated follow-up. Here is what is actually driving the shift.
Leap's pricing starts at around $99/mo and climbs to $200+ once you add the features contractors actually need — digital signatures, product catalogs, custom templates. For a solo roofer or small crew generating 15–20 proposals a month, that's $2,400 a year just to send professional-looking quotes. If you close 30% of those proposals, you're paying roughly $40 per job you win just in software fees. WonTheJob starts completely free with no credit card required, and the paid plan starts at $97/mo with unlimited proposals after the first three. The math is not close.
Leap requires building out a full product catalog before you can send your first proposal. Every material, every line item, every price — entered manually. Contractors report spending 3–5 days on initial setup before generating a single proposal. In that same time, a contractor using WonTheJob has already sent 20 proposals using AI that writes the scope of work from a 30-second voice description. There is no catalog to build. You describe the job, the AI writes the proposal, you send it in 60 seconds. For contractors on the job site, that difference is the difference between winning and waiting.
This is the biggest gap. Leap creates the proposal. That's where it stops. What happens after you send it is entirely up to you — manual calls, manual texts, hoping you remember to follow up in two days. The data on what actually closes jobs is unambiguous: homeowners who don't hear back within 24 hours call another contractor. Over 60% of contractors never send a second follow-up. WonTheJob sends automated SMS follow-ups on Day 1, Day 3, and Day 5 after a proposal is sent — with homeowner name, job type, and a direct link back to their proposal portal. Contractors who enable this feature report winning 20–30% more jobs from proposals they would have otherwise written off.
Marcus, a roofing contractor in Denver, was using Leap for 14 months before switching. His breakdown was direct: "I was spending 45 minutes per proposal — building the quote, adding line items, uploading photos. Now it's 3 minutes. Voice input, AI fills the scope, I review it and send." At 15 proposals per week, that's 10+ hours back per week in proposal time alone. Add the automated follow-up and the time he no longer spends on manual check-in texts, and he estimates 5 hours per week of recovered time. That is half a workday, every week.
WonTheJob is purpose-built for contractors — roofing, HVAC, plumbing, electrical, landscaping, general contracting, kitchen and bath, and concrete and driveway. Every trade gets a distinct proposal template with the right scope language, warranty terms, and compliance language built in. The AI knows the difference between a roofing proposal and an electrical panel upgrade. Homeowners sign electronically from their phone. Follow-up runs automatically. And the whole thing starts free. Contractors leaving Leap are not going to a generic tool — they are going to something built specifically for the trades they work in.
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