Winning enterprise software deals is a high-stakes game, especially for pre-seed and seed-stage companies with limited runway. Every lost opportunity represents time, effort, and money you can’t get back. By understanding why prospects say “no” at each stage of the sales cycle, you can make surgical improvements to your go-to-market motion and increase win rates.

This post will cover the following topics:

• Overall View: Closed-Lost Opportunities by Stage
  • Discovery — 35% of Closed-Lost Opportunities
  • Qualification — 28% of Closed-Lost Opportunities
  • Needs Assessment / Solution Design — 22% of Closed-Lost Opportunities
  • Proposal / Negotiation — 12% of Closed-Lost Opportunities
  • Contract / Closing — 3% of Closed-Lost Opportunities
• Win/Loss Analysis: Why Prospects Make The Choices They Do
  • The Win/Loss Process
  • Win/Loss Themes From Actual Project

Below, we break down the five key sales stages, the percentage of opportunities typically lost at each stage, and the top reasons for those losses.

Overall View: Closed-Lost Opportunities by Stage

1. Discovery — 35% of Closed-Lost Opportunities

Stage Description
The discovery stage is your first real opportunity to uncover the buyer’s needs, challenges, and goals. It’s where you lay the foundation for your entire sales motion. For early-stage SaaS companies, this is often the moment to position your solution against bigger, more established competitors by focusing on niche strengths. A failure here means you may never get the chance to present a compelling proposal.

1. Poor discovery / Not understanding buyer needs (45%)

Many founders and sales teams rush discovery, asking surface-level questions or following a rigid script instead of engaging in deep, consultative conversations. For 45% of lost deals at this stage, the problem is that the seller never truly grasps the buyer’s underlying pain points. Without a clear understanding, the product pitch ends up generic, misaligned, and easy to dismiss. Early-stage CEOs should train their teams to go beyond features and actively map the buyer’s operational, financial, and strategic goals, ensuring the solution’s value proposition directly addresses the real business problem.

2. Lack of stakeholder engagement / Missed decision-makers (35%)

In 35% of lost discovery-stage deals, the seller engages only one or two contacts and fails to reach critical decision-makers. In enterprise sales, missing the CFO, CTO, or key department heads can doom your opportunity before it matures. Competitors who build multi-threaded relationships often win simply by being more present in internal discussions. For early-stage SaaS teams with limited resources, this means proactively mapping the buying committee early and using every conversation to expand your reach inside the account.

3. Prospect not ready / Early in buying journey (20%)

About 20% of discovery-stage losses happen because the prospect is not in an active buying cycle. The need may be real, but the urgency is missing. While these deals may not close now, they can be future opportunities if nurtured properly. For early-stage CEOs, it’s important to create a structured process for re-engaging such prospects — whether through thought leadership, quarterly check-ins, or targeted marketing touches — so that when the need becomes urgent, your brand is top of mind.

2. Qualification — 28% of Closed-Lost Opportunities

Stage Description
Qualification is where you determine whether the opportunity is worth pursuing. This involves assessing budget, authority, need, and timing (BANT) or similar frameworks. For early-stage SaaS companies, pursuing unqualified leads can drain resources, while disqualifying too aggressively may cause you to miss strategic wins.

1. Budget constraints / No allocated funds (55%)

The single biggest killer in qualification — responsible for 55% of losses here — is discovering that the prospect simply doesn’t have the budget. Sometimes this is about timing (mid-year freezes), but often it reflects a lack of perceived urgency or value. Early-stage CEOs should focus on teaching teams how to tie the solution directly to cost savings, revenue generation, or regulatory compliance, making it easier for prospects to reallocate funds even in lean times.

2. No executive sponsorship / Lack of authority (30%)

About 30% of qualification-stage losses come from engaging with someone who can’t actually approve the purchase. This often happens when founders or SDRs are happy to talk to anyone showing interest but fail to move upward in the org chart. The fix is to establish “power contact” criteria and equip salespeople with language and tools to request introductions to decision-makers early.

3. Low strategic fit / Wrong market segment (15%)

For 15% of losses here, the product simply isn’t aligned with the buyer’s strategic priorities. This could be due to targeting the wrong industry vertical or size segment. Startups often chase inbound leads outside their ICP to fill pipeline numbers, but this can result in wasted cycles. Tight ICP definition and enforcement help prevent this.

3. Needs Assessment / Solution Design — 22% of Closed-Lost Opportunities

Stage Description
This stage is where your product vision meets the client’s technical and functional requirements. It’s your chance to customize the offer and show you understand their unique workflows. For early-stage SaaS companies, winning here can prove credibility even against bigger competitors.

1. Solution doesn’t meet technical requirements (50%)

Half of all losses here happen because the product simply can’t meet critical technical specifications. This could be due to integrations, security requirements, or scale limitations. For early-stage CEOs, transparency is key — overpromising and underdelivering destroys trust. Instead, focus on clearly articulating your roadmap, offering phased rollouts, or partnering with complementary solutions.

2. Weak differentiation / Competitor offers better fit (30%)

In 30% of cases, prospects feel a competitor’s solution aligns better with their needs. This often stems from a lack of clear competitive positioning. Early-stage founders should arm their teams with competitive battle cards that highlight unique capabilities, customer success stories, and measurable ROI that others can’t match.

3. Misaligned priorities / Internal project delays (20%)

For 20% of lost deals here, the issue isn’t the solution itself but shifting priorities inside the buyer’s organization. Economic shifts, leadership changes, or urgent new projects can push your initiative down the list. Maintain momentum by regularly reinforcing the business impact of your solution and adapting timelines when needed.

4. Proposal / Negotiation — 12% of Closed-Lost Opportunities

Stage Description
Here, you’ve earned the right to present pricing, terms, and an implementation plan. This is a pivotal moment where confidence, flexibility, and perceived value collide.

1. Price objections / ROI not demonstrated (60%)

Price is the number one reason for losses in this stage, accounting for 60% of cases. Often, it’s not that your price is too high — it’s that your value isn’t fully understood. Early-stage CEOs should coach teams to connect every pricing conversation to hard ROI metrics and customer outcomes.

2. Contract terms / Legal issues (25%)

In 25% of cases, deals stall or die in legal review. This can be due to unfavorable liability clauses, IP terms, or data privacy requirements. Founders should work with legal advisors early to develop startup-friendly yet enterprise-acceptable contract templates.

3. Procurement delays (15%)

About 15% of losses happen when deals get bogged down in lengthy procurement processes. This can be mitigated by understanding the buyer’s process early and proactively aligning timelines.

5. Contract / Closing — 3% of Closed-Lost Opportunities

Stage Description
The final step is often assumed to be a formality, but last-minute disruptions can still derail deals.

1. Last-minute budget cuts / freezes (40%)

Economic uncertainty or company-specific downturns can cause sudden budget freezes. Early-stage SaaS leaders should keep multiple champions engaged to ensure the deal doesn’t depend on a single approval.

2. Internal leadership changes (35%)

New executives often pause or cancel deals to reassess priorities. Maintaining broad stakeholder engagement can help survive leadership transitions.

3. Contract expiration / Lapsed timelines (25%)

Deadlines slip, and momentum is lost — especially if buyer priorities shift. Establish clear, close plans with mutual accountability to avoid deals going stale.

Win/Loss Analysis: Why Prospects Make The Choices They Do

The Win/Loss Process

Win-Loss Analysis is a market research technique that companies can use to gain key insights from customers and prospects. These learnings can then drive improvements in marketing and sales, leading to increased revenue and profits. A typical Win/Loss project consists of five major steps:

DevelopentCorporate

1. Planning

The first step in the process is to complete all preparatory work necessary to ensure the project’s success. A crucial first step is to set research objectives. Setting clearly defined Research Objectives will help you both target your Win/Loss research and set expectations for the program’s success.  And be sure to align your Research Objectives with the strategic goals of your organization. There is no sense chasing information from buyers that your organization has no interest in anyway. Research objectives may include:

• Your Product-Market-Price fit
• New market problems that your organization can solve
• Your service levels
• Persona refinement
• Buyer purchase-decision process
• Marketing channel effectiveness
• Sales process
• Communication style
• A better understanding of your place in the competitive mix

In addition to establishing your Research Objectives, you should also define the questions that will be asked during the interviews. The questions should be open-ended and designed to encourage a free-flowing discussion.

Finally, you will need to design the process you will use to recruit potential interviewees, conduct the interviews, analyze, and report the results you have learned. The plan should lay out the roles and responsibilities of each participant in the project. You should also develop a schedule and a simple status reporting mechanism so everyone can stay up to date. Create a project charter that contains the research objectives, interview questions, roles, responsibilities, and schedule. Conduct a review meeting with the participants to approve and commit to the plan.

2. Recruitment

The next step in the process is to recruit people for the interviews. Most companies target a mix of net new customers and existing customers who have upgraded or expanded their use of products. You are looking for a mix of won deals and lost deals. Most Win/Loss Analysis projects with a single research objective try to get 15 to 20 interviews.

A portfolio approach to soliciting interviews works best. The tactic that has the highest success rate is when a salesperson makes a personal outreach to a potential interviewee. Generally, 25% to 40% of these contacts will convert to an interview. The second most common approach is email. Organizations pull a list of candidates from their CRM or sales force automation system and then email them asking for participation in the project. This approach performs like most email campaigns – a 20% open rate and a 2% to 5% click-thru rate. 50% of those who click-thru convert to interviews. The final tactic is to do phone follow-up with contacts that opened the email but did not click thru. This tactic performs like telemarketing campaigns, a 1% to 2% success rate.

Most Win/Loss Analysis programs use incentives to encourage targets to commit to doing the interview. Companies offer a $25 or $50 gift card. This provides the interviewee with something tangible in exchange for their valuable time.

The biggest challenge many Win/Loss Analysis projects face is recruiting enough quality interviewees. Sending cold non-personalized emails to all of the CRM contacts associated with a customer tends not to be successful. What happy customer wouldn’t want to do a short interview and get a $50 VISA gift card? A lot fewer than you would expect. Experience has shown that a portfolio approach that combines warm introductions, multiple emails, and follow-up phone calls works best.

Sometimes, a Win/Loss Analysis project encounters difficulties in obtaining sufficient interviews to meet the research objectives. Teams will then increase the interview incentive to $75 or even $100. While this may spur more people to respond to the solicitation, often these individuals are only interested in the incentive payment. These individuals may only have limited exposure to the product and may not have been involved in the actual sales process. This risk can be mitigated by selecting the most suitable candidates to target with the solicitation. Sending an email blast to every contact from a company in your CRM system will not produce the quality results you are looking for.

3. Interviews

The core activity of the project is conducting interviews. Most interviews take 20 to 30 minutes to complete. Companies use internet meeting services that facilitate the interview scheduling process, but also allow the discussion to be recorded. This enables the interviewer to focus on the discussion instead of trying to listen and take notes simultaneously. There are services that will transcribe the recordings for you into a Word document for about $1 per minute.

Experience has shown that interviewees are more comfortable speaking with an independent third party rather than a representative from the company. This results in a free and easy discussion. It also avoids making embarrassing or disparaging comments about their experiences or opinions.

A critical aspect of the interview process is asking why a customer believes certain things they say. Surveys and checklists are one way to get customer feedback, but they lack the ability to follow up on interesting statements. The real value of using experienced interviewers is that they can follow up and explore why a customer believes specific things. Often, this is the most valuable outcome from the interviews.

4. Analysis

After the interviews are completed, the recordings are transcribed. Next, the team reviews the transcripts to identify common themes. These themes are analyzed and documented in a final report. The report contains a summary of the interviewees – company size, interviewee title, transaction type (new/upgrade and win/loss). For each theme or finding, specific quotes from the interviews are included. This lets the report’s reviewers hear, from the customer’s perspective and in their voice, the exact point they were trying to make. A meeting is held with all of the interested internal organizations to review the report’s findings and conclusions.

5. Action

The final step is to take action on the recommendations. Effective Win/Loss Analysis programs are really part of a cycle to drive improvements in the business. Win/Loss Analysis is a variant of the Six Sigma DMAIC (Define, Measure, Analyze, Improve, and Control) methodology. If action is not taken based on the recommendations from the interview analysis then an opportunity to fundamentally improve your business will be missed.

Win/Loss Themes From Actual Project

Themes are the learnings distilled from the Win/Loss interviews.  Here are some examples from a Marketing Automation SaaS provider: For reference, the Marketing Automation SaaS provider had been in business for over eight years.  They had over 3,500 active customers.  Top line revenue was around $50 million.  They were VC-funded, having recently raised over $20 million in a Series C round.  Most of their inbound leads came from the web.  Their product was considered to be a market leader in terms of functionality.

Fifteen interviews were conducted from ‘win’ transactions.  5 were from net new customers, 10 were from existing customers.. 6 were from mid-market organizations with less than $100 million in revenue. * were from enterprises with revenues between $100 million and $2 billion.  The major themes included:

Positive Themes from Interviews

Thought Leadership.  The vendor was regarded as a thought leader in the industry.  Almost all interviewees cited the quantity and quality of thought leadership articles the vendor published.  The readers liked that the vendor did not push their products in these articles.

Functionality.  All the interviewees cited the depth and quality of the product’s features and functions.  Many felt that competitors fell short in a few key areas.

Sales Team Effectiveness.  Many interviewees cited the professionalism, responsiveness, and courtesy of the sales teams.  They did not feel pressured or subjected to typical software sales techniques (buy before the end of the quarter to avoid a price increase).

Analyst Reports.  Many interviewees cited the inclusion the Leaders Quadrant in Gartner Group’s Marketing Automation Magic Quadrant as being important.

User Reviews.  Some prospects/customers cited the multitude of reviews on user review sites like G2.com and Capterra.

Negative Themes from Interviews

Price.  Most interviewees considered the price for the SaaS solution to be among the highest in the industry.  Many competitors had better pricing.

Packaging/Commercial Terms.  The majority of the ten existing customers cited dissatisfaction with the product packaging.  Most were satisfied with the entry-level offering but were very dissatisfied with upgrade options.  Many felt that the upgrade packages included add-on products that offered little to no value.  The pricing was based on the number of modules purchased and a transaction limit.  The entry-level offering had three modules and 10,000 transactions a month.  Transactions above 10,000 were billed at  $0.05 a transaction.  The smallest upgrade was four times the cost of the entry-level package.  The upgrade included six additional modules and 25,500 transactions a month.  Customers rejected the upgrade 80% of the time.  They saw little value in the extra modules and rejected the effective per-transaction price increase.  Many customers moved to a solution that offered significantly lower transaction costs but also had less functionality.  They accepted the trade-off.

Change in Priorities.  Many loss transactions were due to a change in customer business priorities.  The need to focus on another issue was more important than investing in the vendor’s solution.

No Perceived Differentiation.  The prospect was unable to see a real difference in value between competing solutions.  While competitive solutions had clearly lower levels of features/functions, the prospects were unable to see any real difference.  Lower prices trumped what appeared to be better functionality.

Disruptive Events.  Events like mergers, acquisitions, divestitures, or departures of key executive sponsors often delay or cancel planned purchases.

No Decision.  The most common reason cited for lost deals was ‘No Decision’.  Either the prospect/customer never made a decision, or the vendor was unable to determine why the sales process stopped.

Conclusion: Turning Lost Deals into Future Wins

For pre-seed and seed-stage SaaS CEOs, understanding why deals are lost at each sales stage is more than a sales exercise — it’s a growth strategy. Every “no” contains valuable insights that can refine your ICP, sharpen your competitive positioning, and improve win rates. By leveraging structured win/loss analysis, early-stage founders can identify the root causes of lost opportunities — from poor discovery to misaligned proposals — and turn them into repeatable wins.

The fastest-growing SaaS companies don’t just track pipeline metrics — they act on them. If you consistently analyze closed-lost data, engage decision-makers early, and align your value proposition to urgent buyer needs, you’ll shorten sales cycles, increase close rates, and maximize your limited runway.

Your next big win isn’t just about finding more leads — it’s about learning from the ones that got away. Start applying these insights today to build a sales process that wins more deals, more often.

Also published on Medium.