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Introduction
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Captcha
What's your average sales cycle for mid-market deals ($50K-$200K ACV)?
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Under 30 days
30-45 days
45-60 days
60-90 days
90+ days
Be honest about actual cycle time from first conversation to signed contract, not your target or what you tell investors.
What percentage of qualified opportunities die during technical validation, POC, or implementation planning?
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Less than 5%
5-10%
10-20%
20-30%
30% or "I don't actually track this"
Think about deals that made it past initial interest but stalled when prospects started asking technical questions or testing your platform.
How often do enterprise prospects ($200K+ ACV) ask questions about your platform architecture, integration capabilities, or technical roadmap that stall the deal?
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Rarely or never
Occasionally - but we can address them
Frequently - requires executive escalation
Almost always - we lose deals because of it
We've stopped pursuing enterprise deals because of this
Consider questions like: "Can your platform handle our data volume?" "What's your uptime SLA?" "How do you handle data residency?" "Can we see your security architecture?"
What percentage of your engineering team's time goes to firefighting (production incidents, emergency fixes, maintenance, integration failures) vs. building new features?
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20% firefighting / 80% building
30-40% firefighting / 60-70% building
50-50 split
60-70% firefighting / 30-40% building
70%+ firefighting or "I don't actually know"
Firefighting includes: fixing bugs, emergency patches, responding to incidents, maintaining integrations, addressing technical debt, "keeping the lights on."
How many production incidents (customer-impacting outages, data failures, integration breaks) do you have per month?
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Less than 2 per month
2-4 per month
5-8 per month
8-12 per month
12+ per month or "Multiple per week"
Count incidents that required customer communication, emergency fixes, or caused visible service degradation.
How often do your largest customers complain about slow response times, downtime, or integration failures?
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Rarely or Never
Occasionally (a few times per quarter)
Monthly
Weekly
Daily / Constantly
Include tickets, escalations, or conversations where technical issues were raised as a concern.
What percentage of your ARR is at risk due to pending churn (customers in renewal conversations, contracts up soon, or dissatisfied)?
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Less than 5%
5-10%
10-20%
20-30%
30% or "I don't actually know"
Be realistic about customers who haven't renewed yet, or who you're worried might not renew.
How often does your product or engineering team miss committed roadmap deadlines?
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Rarely - we hit 90%+ of commitments
Occasionally - we hit 70-80%
Frequently - we hit 50-60%
Constantly - we miss more than we hit
We stopped making commitments because we can't predict timelines
Count commitments made to customers, sales, or leadership that slipped significantly.
When a new customer asks for an integration or custom feature, how long does it typically take?
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Under 2 weeks
2-4 weeks
4-8 weeks
2-3 months
3+ months or "We can't predict it"
How confident are you in your platform's ability to scale 10x from here?
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Very confident - we're built to scale
Mostly confident - minor concerns
Somewhat confident - several known bottlenecks
Not confident - major architectural concerns
We'd break immediately
Consider database performance, API reliability, infrastructure costs, and team capacity.
Has your technical debt or platform instability already cost you a deal, delayed a fundraise, or triggered executive departures?
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No - hasn't happened yet
Almost - came close but dodged it
Yes - cost us one deal or hire
Yes - cost us multiple deals/hires
Yes - it's actively killing our business
Be honest about deals lost to competitors with better tech, fundraises that stalled in due diligence, or key people leaving due to product frustration.
If you raised your next round tomorrow, how much of it would go to fixing technical problems vs. growth?
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Less than 10% to fixes
10-20% to fixes
20-30% to fixes
30-50%
50%+ to fixes / we can't raise until we fix this
Include platform rewrites, infrastructure upgrades, technical debt paydown, and reliability improvements.
What % of your target customers would be 'very disappointed' if your product disappeared?
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60%+ (Strong PMF)
40-60% (Solid PMF)
20-40% (Emerging PMF)
Under 20% (Weak PMF)
I don't know / Haven't measured
This metric reveals true product-market fit. 40%+ indicates strong customer dependency. Be honest about what customers actually say, not what you hope they'd say.
What % of new customers come from referrals or word-of-mouth?
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50%+ (Strong organic growth)
30-50% (Healthy referrals)
10-30% (Some referrals)
Under 10% (Weak referrals)
I don't track referral source
High referral rates (40%+) indicate strong PMF and customer satisfaction. Low rates suggest you're pushing products customers don't love.
What is your current monthly net revenue retention (NRR) rate?
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110%+ (Exceptional)
100-110% (Strong)
90-100% (Acceptable)
Under 90% (Concerning)
I don't track this metric
NRR measures revenue retention from existing customers after accounting for churn and expansion. 100%+ means you're growing from existing customers. 95%+ is healthy for most SaaS.
How many significant product iterations have you made based on customer feedback in the last 6 months?
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10+ iterations (Highly responsive)
5-10 iterations (Active learning)
3-5 iterations (Moderate pace)
1-2 iterations (Slow adaptation)
0 iterations or I don't track this
Iteration velocity shows you're listening to customers and adapting. 5+ iterations suggest active learning. 0-2 suggests you're not incorporating feedback effectively.
What % of your ideal customer profile (ICP) can you reach with your current go-to-market strategy?
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80%+ (Dominant reach)
60-80% (Strong reach)
40-60% (Moderate reach)
20-40% (Limited reach)
Under 20% or unclear ICP definition
Strong PMF means you can efficiently reach most of your target market. 60%+ reachability indicates scalable distribution. Under 30% suggests GTM challenges that will limit growth.