Selling a Cloud Software business

This is based on hundreds of real buyer-seller due diligence conversations we’ve helped happen on Rejigg. These are the Cloud Software topics that move price and terms quickly: how you define recurring revenue, what actually drives retention, how renewals get done, how hosting costs behave, and whether the company runs without founder heroics.

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What buyers evaluate, and how to prepare

What counts as ARR in your reporting, and can you tie it back to your billing system?
Deal-critical
ARR Truth

What buyers determine

Buyers are checking whether your headline ARR is real, repeatable, and easy to audit. They want Stripe or your billing tool, invoices, credits, refunds, collections, and your reported ARR to line up without hand-wavy spreadsheet math. If ARR means different things in different places, they usually slow the deal down and protect themselves on price or terms.

How to prepare

  • Write a one-page ARR definition that includes and excludes implementation fees, one-time charges, credits, and pass-through usage
  • Build a customer-level ARR roll-forward: starting ARR, new, expansion, contraction, churn, ending ARR
  • Export customers with plan, price, start date, renewal date, and last invoice date. Reconcile the export to total ARR
Great answer
We define ARR as contracted subscription fees only. Implementation and one-time work are excluded, and usage overages are tracked separately as variable revenue. Here’s our customer-level ARR roll-forward for the last 12 months, plus the billing export it ties to, including credits, refunds, and write-offs.
Good answer
We can pull ARR from the billing system and explain a few manual adjustments, but we haven’t built a clean end-to-end roll-forward yet.
Red flag
ARR is what the dashboard says. We mix usage, services, and subscriptions, and we can’t cleanly tie the number back to invoices and collections.
How Rejigg helps:Rejigg’s secure data room lets buyers review billing exports, roll-forwards, and reconciliations in one place without email back-and-forth.
Do your retention numbers mean what buyers think they mean, and what’s driving net revenue retention?
Deal-critical
Retention Drivers

What buyers determine

Buyers are trying to understand whether customers stick around because the product is truly embedded, or because your team keeps saving accounts at the last minute. They will look at retention by cohort, downgrade patterns, and whether expansion is coming from healthy adoption or a few big accounts swelling. Averages can hide problems. Cohorts show the truth over time.

How to prepare

  • Produce retention by cohort (start month or quarter). Explain any periods where performance shifted, and why
  • Break net revenue retention into expansion sources like seats, usage, modules, and price changes
  • Create a churn and downgrade log for the last 20–50 events with one primary reason and a sentence of context
Great answer
Net revenue retention is 118% over the last 12 months. Expansion is mostly seat growth in mid-market, plus a second module in about a third of those accounts. Here are cohort charts by start quarter. You can see the Q3 onboarding cohort improved after we changed the first-week activation flow, and we usually see renewal risk show up in usage 45–60 days ahead.
Good answer
We know our net retention and gross churn and can talk through churn reasons, but our cohort view and downgrade tracking still need work.
Red flag
Churn is low, and net retention is high. We don’t track cohorts or downgrades, and we can’t explain why customers expand beyond “they like the product.”
How Rejigg helps:Rejigg helps you share retention work in a consistent format and answer follow-ups in direct messaging so definitions stay consistent across buyers.
Are renewals actually predictable, or do they slip until the last minute?
Deal-critical
Renewal System

What buyers determine

Buyers want to see recurring revenue run like a process, not a series of rescues every quarter. They look for clear ownership, a consistent timeline, and renewal risk that is spread out rather than stacked into one scary month. If you keep renewing in the final week, they assume hidden churn risk, even if your historical churn looks fine.

How to prepare

  • Create a 12-month renewal calendar with ARR up for renewal by month, highlighting top accounts
  • Document your 120/90/60-day renewal steps and name who owns each step
  • Add one health signal for each top account, like usage trend, open tickets, payment history, or champion status
Great answer
Renewals are owned by our CS (Customer Success) lead. At 120 days, we confirm stakeholders and success criteria; at 90 days, we review usage and open risks; and at 60 days, we line up legal and procurement. Here’s the next 12 months of renewals with top accounts and health notes. We also track on-time renewal rate and can show what slips, and why.
Good answer
We have a renewal calendar and a rough process, but it’s not consistently followed, and we still end up doing a few last-minute saves each quarter.
Red flag
Renewals are automatic until they aren’t. We usually start working them when the customer pings us, or we notice the contract is about to end.
How Rejigg helps:Rejigg keeps buyer conversations organized and lets you share renewal schedules in stages after NDAs are signed.
Are there any side letters, non-standard terms, or handshake promises tied to key accounts?
Deal-critical
Contract Risk

What buyers determine

This question is about unpleasant surprises hiding in “special” customer deals. Buyers are looking for extra support promises, custom build commitments, odd refund language, and termination terms that make revenue less durable than it looks. They also want to know whether auto-renew works in practice, or whether every renewal reopens the full negotiation. One messy top-customer contract can change price, escrow, or structure.

How to prepare

  • Summarize your typical term length, auto-renew language, termination rights, and renewal notice windows in plain English
  • List non-standard obligations for top customers, including special support and feature commitments
  • Document how pricing exceptions are approved and how often you discount or concede at renewal
Great answer
Most customers are on 12-month terms with auto-renew and standard termination language. For our top 15 accounts, here’s a one-page list of any non-standard clauses, side letters, or extra support and feature commitments. We also track renewal concessions, so we can show how often we discount to retain an account and what triggers it.
Good answer
We believe most contracts are standard and can pull exceptions if asked, but we don’t have a consolidated list of side letters and special obligations yet.
Red flag
It’s all in the contracts somewhere. If we promised anything extra, it’s probably in email threads, but it hasn’t caused issues.
How Rejigg helps:Rejigg’s data room lets you share contracts and an exceptions list cleanly, without turning diligence into an email scavenger hunt.
Is your revenue truly SaaS, or is a chunk of it really services wearing a subscription hat?
Deal-critical
Services Creep

What buyers determine

Buyers are fine with services revenue. They just value it differently because it scales with people, not software. If the “subscription” quietly includes custom reporting, unpaid implementation, or ongoing admin work, your margins and growth story are usually weaker than the P&L suggests.

How to prepare

  • Split revenue per customer into subscription, usage, professional services, and one-off items
  • Show the last 10 implementations with a time-to-go-live date, internal hours by role, and what was standard versus custom
  • Estimate customer-level gross margin for your top 20 accounts, even if it’s directional
Great answer
For our top 20 accounts, we split subscription versus services and estimate gross margin by customer. Mid-market implementations average two weeks using a standard playbook, and custom work is scoped and billed. Support boundaries are documented, and recurring admin work is either productized or charged as services.
Good answer
We can describe implementation and support workload and show examples, but we haven’t quantified internal hours or customer-level margin yet.
Red flag
Implementation varies a lot. We do whatever it takes to get them live, and support is basically unlimited because we don’t want churn.
How Rejigg helps:Rejigg lets you package implementation data and customer revenue mix so buyers can see what’s product revenue versus people-heavy work.
What drives hosting costs, and where are the margin cliffs as usage grows?
Deal-critical
Infra Margins

What buyers determine

Cloud COGS often surprises buyers because the cost drivers can be scattered across compute, data storage, logging, data egress, and third-party APIs. They want to know whether growth improves margins, holds steady, or gets worse as customers use the product more. They also care about spike risk, like one enterprise customer tripling usage in a week.

How to prepare

  • Break down hosting and vendor costs by driver and tie each driver to a usage metric you track
  • Map which features trigger variable costs and show how pricing and packaging cover them
  • Identify the biggest cost drivers by customer or segment and document mitigation plans like caching or vendor renegotiation
Great answer
We tie infrastructure spend to active users and API calls, and we track cost per active customer by segment. Here’s a feature-to-cost map for logging, messaging, and data egress, and how our pricing covers each. We also flag the top three high-usage accounts and can show margin impact under a usage spike scenario.
Good answer
We know total cloud spend and the biggest vendor bills, but we can’t consistently tie costs back to usage drivers yet.
Red flag
Here’s our AWS bill. We assume margins improve with scale, but we haven’t analyzed which features or customers drive spend.
How Rejigg helps:Rejigg’s data room gives you a secure place to share vendor invoices and cost-driver work only after a buyer is vetted and under an NDA.
If you were the buyer, what security and privacy risks would you want disclosed up front?
Deal-critical
Security Posture

What buyers determine

Security diligence is about what risk the buyer is inheriting. Buyers want proof you control production access, handle incidents competently, and can meet the security promises you already made to customers. If you sell into regulated industries or enterprise IT environments, security maturity can expand or shrink the buyer pool and affect deal terms.

How to prepare

  • Prepare a security packet: production access list, access onboarding and removal steps, logging approach, and incident response basics
  • Summarize past incidents, what changed afterward, and what controls you tightened
  • Collect recent security reviews or pen test summaries and list what customer security requirements you can support today
Great answer
Here’s our security packet with who has production access, how access is granted and removed, and how we log and review changes. We had one material incident last year, detected through monitoring, remediated within hours, and we implemented specific controls afterward that we can walk through. We can also share the latest third-party security review summary and what we fixed.
Good answer
We don’t have a formal certification, but we can explain access controls, incident handling, and the security questionnaires we regularly pass.
Red flag
We haven’t had issues, so we haven’t built much process around security. We can handle it if a buyer asks.
How Rejigg helps:Rejigg’s buyer vetting and digital NDAs let you share sensitive security materials only with credible buyers at the right point in the process.
Is the product defensible as-is, or is there a rewrite waiting to happen?
Important
Tech Risk

What buyers determine

Buyers are estimating the engineering effort required post-close to keep uptime stable and keep shipping. They look for fragile dependencies, how releases are handled, incident history, and whether the system is held together by tribal knowledge. Clear tech debt with a realistic plan usually lands well. Surprise rewrites found late tend to change price or timelines.

How to prepare

  • Write a one-page architecture overview a smart non-engineer can follow, including tenancy and data flow
  • Document deployment and release practices, and summarize incident history with the key learnings
  • List the top technical risks with a realistic fix plan, including rough timing and who would do the work
Great answer
Here’s our one-page architecture overview, how tenants are separated, and how deployments work. These are the top three technical risks we’d fix in the next 6–12 months, plus the expected effort and why it matters. We can also walk through incident history and the monitoring and release changes we made after each one.
Good answer
We can describe the architecture and where tech debt lives, but we don’t have a clean written narrative or a prioritized plan yet.
Red flag
It works, and we haven’t had major issues. We don’t track incidents or maintain a list of technical risks.
How Rejigg helps:Rejigg helps you share architecture and incident materials in a controlled way so technical diligence doesn’t turn into random document requests.
What are the “hidden jobs” you still do that keep renewals, releases, and escalations moving?
Important
Owner Dependence

What buyers determine

In Cloud SaaS, founder dependence often shows up in decision bottlenecks. Pricing exceptions, roadmap trade-offs, renewal escalations, release approvals, and security responses can all quietly route through the founder. Buyers want to know the team can run those moments without you. If they can’t, buyers usually protect themselves with longer transitions, retention packages, or performance-based payouts.

How to prepare

  • List the recurring decisions you personally make each week and what triggers them
  • Assign a named owner for each decision, and run the handoff for a few cycles
  • Document escalation paths for outages, renewals, and security questionnaires so the team can run without you
Great answer
I documented the recurring decisions I used to own: pricing exceptions, renewal escalations, release go/no-go, and security questionnaires. Each one has a named owner now, and we’ve run it that way for two quarters, with me stepping in only for true edge cases. Here’s our escalation path and what ownership looks like post-close.
Good answer
I’m still involved in a few big decisions, but we’ve started handing off renewals and release approvals, and it’s improving.
Red flag
The team is strong, but most big calls still come to me because I know the customers and product best.
How Rejigg helps:Rejigg helps you set transition expectations early and keeps buyer questions in one place so your day-to-day role is clearly understood.
Is go-to-market a system, or a set of one-off wins that won’t repeat?
Good to have
Growth Motion

What buyers determine

Buyers are looking for evidence you can keep creating new ARR efficiently after the sale. They want to understand your motion, whether that’s product-led signups and upgrades, or demo-led sales with security reviews and procurement cycles. A clean, repeatable funnel story can lift valuation. It rarely rescues a deal if retention is weak.

How to prepare

  • Share a funnel snapshot that matches your motion, such as trial-to-paid, demo-to-close, outbound-to-meeting, or partner-sourced to close
  • Break down lead sources and explain lumpiness in plain English, including partner batching or budget-cycle timing
  • Show a few real expansion stories and why they happened, including product triggers and CS actions
Great answer
Our motion is product-led for SMB and demo-led for mid-market. Here are the last 90 days of funnel metrics by segment, and conversion and cycle length are stable. We can also share three specific expansion stories, including the feature that drove adoption and the CS touch that pulled it forward.
Good answer
We know where leads come from and what closes, but we don’t have a consistently tracked, segmented funnel snapshot yet.
Red flag
Growth is mostly referrals and momentum. We don’t track the funnel, but we think there’s a lot of upsell potential.
How Rejigg helps:Rejigg connects you with vetted SaaS buyers and makes it easy to run direct calls to see which growth story holds up under questions.

Straight from buyer evaluations

“Two decades of customer retention and huge amounts of data embedded in client accounts. When switching away would mean losing all of that, you know the revenue is real and customers aren't going anywhere.”
Customer LoyaltyBuyer impressed by customer stickiness at a SaaS platform
“Existing customers keep expanding their usage over time without anyone having to sell them. The product grows naturally inside each account. That's the kind of built-in growth you can't fake.”
Natural GrowthBuyer reviewing expansion patterns at a cloud software company
“Their technology costs were under 15 percent of revenue with a clean, modern setup. That tells me the engineering team knows what they're doing and the profits will hold as the business grows.”
Efficient TechnologyBuyer analyzing technology costs at a SaaS platform
“Every customer was on an annual contract that renews automatically, and the product is woven into how they work every day. That's not software people cancel on a whim. It's part of their routine.”
Reliable RevenueBuyer reviewing contracts and usage at a cloud software company
“The engineering team ships updates every week without the founder reviewing every change. That told me more about how mature this business really is than any spreadsheet could.”
Team IndependenceBuyer evaluating team independence at a SaaS company

How buyers value this type of business

Where you land in that range depends on how much of your revenue renews automatically, how long customers stay, and how much the business runs without you.

3x–8x
annual profit
Depending on recurring revenue, retention, and team independence

What drives a premium

  • Customers who stay and expand their usage
    When existing customers naturally use more of your product over time, buyers see built-in growth that doesn't require a sales team to push.
  • Very few customers leaving
    Low cancellation rates prove customers genuinely rely on your product, not just that they haven't gotten around to cancelling.
  • Revenue spread across many customers
    When no single customer makes up a huge chunk of your income, the business feels much safer to buyers.
  • A product customers use every day
    Software that's embedded in how customers work creates natural loyalty because switching would disrupt their daily routine.
  • Technology costs that stay manageable
    Keeping hosting and infrastructure costs well managed shows the business stays profitable as it grows.

Common add-backs

Your salary above what you'd pay a product or engineering leaderOne-time development or technology projects that won't continueSetup fees that were bundled into subscription pricingConsulting or project work that isn't part of the core product

What the process looks like

5–8 months from listing to closemedian 201 days across closed deals
  1. 1
    Listing
    The day your business goes live on Rejigg.
  2. 2
    First messageMedian: 4 days later
    A buyer requests a conversation by sending a first pitch.
  3. 3
    First callMedian: 7 days later
    Your first completed call with a buyer to answer questions about your business.
  4. 4
    Letter of intentMedian: 59 days later
    A buyer submits an LOI and you choose to accept, decline, or negotiate.
  5. 5
    Deal closeMedian: 89 days later
    Assuming all is well in due diligence, you close the deal.
See the data behind this timeline in the 2026 Insight Report
Typical buyer types
Investment firms building a portfolio of software companiesLarger software companies looking to expand into your market or customer baseIndividual operators with technical or industry backgrounds who want to own a businessPlatform companies looking to add your product to their existing suite

Common questions about selling a Cloud Software business

Most Cloud Software businesses are valued using a multiple of profit, then buyers adjust based on retention and gross margin quality. Buyers pay more when renewals are predictable, customers expand over time, and hosting plus vendor costs stay controlled as usage grows. Start with Rejigg’s <a href="/valuation" style="color: #1d4d05; font-weight: 600;">free valuation calculator</a>, then pressure-test the result against customer concentration, renewal calendar risk, and any services work buried inside “subscriptions.”
Net revenue retention and churn affect multiples because they change how much future ARR a buyer can count on. Strong cohort retention and steady expansion usually support a higher price and fewer protections in the deal. Weakening cohorts, rising downgrades, or churn concentrated in one segment often leads to a lower multiple, holdbacks, or an earnout tied to retention. Bring cohort charts and a churn log so the buyer isn’t guessing.
Yes. You don’t need a broker to sell a Cloud SaaS company, and paying 5–10% of the sale price is hard to justify when you can run a direct process yourself. Rejigg gives you buyer access, pre-vetted inbound interest, digital NDAs, a secure data room, and deal tracking so you can manage outreach, diligence, and offers without a middleman. Start with the <a href="/owners/owners-guide/find-your-dream-buyer" style="color: #1d4d05; font-weight: 600;">finding buyers guide</a>.
Usually, no. Most small and mid-sized Cloud Software deals close without audited financials, but buyers do expect numbers that reconcile back to your billing system. If your reported ARR cannot be tied to invoices, credits, refunds, and collections, that creates more drag than the lack of an audit. Clean billing exports and a customer-level ARR roll-forward usually matter most. Rejigg’s QuickBooks integration can help you build a cleaner data room without spreadsheet sprawl.
Many Cloud Software deals use cash at close plus seller financing or an earnout, especially when the buyer wants protection against retention risk. For steadier subscription businesses with clean financials, some buyers also use SBA 7(a) loans, and those lenders will focus on churn stability and owner add-backs. If you want to model the payment math before negotiations, use Rejigg’s <a href="/sba-calculator" style="color: #1d4d05; font-weight: 600;">SBA loan calculator</a>.
Most Cloud SaaS sales take 3–8 months from getting your story and data organized to closing. Timelines stretch when buyers cannot reconcile ARR to billing, when renewal risk is unclear, or when security and technical diligence uncover surprises late. A staged data room and regular buyer updates usually keep momentum. Rejigg’s <a href="/owners/owners-guide/due-diligence-and-closing" style="color: #1d4d05; font-weight: 600;">due diligence checklist</a> helps you avoid the common time-wasters.
An ARR roll-forward shows how recurring revenue changed over a period using a simple bridge: starting ARR, new sales, expansion, contraction, churn, and ending ARR. Buyers insist on it because it forces your ARR to match customer-level reality, not a dashboard number that cannot be explained. If the bridge does not tie out, buyers assume data quality issues and start discounting everything. Keep the roll-forward and the billing export together in your data room.
Common terms include a working capital true-up at closing, legal promises about customer contracts and security incidents, and a holdback or escrow to cover post-close surprises. Earnouts are also common when the buyer wants the price to depend on retention or ARR after the handoff. Terms are usually a response to a specific risk, like renewal concentration or a security remediation plan. Push for clear definitions so you are not negotiating vibes.
A working capital adjustment is a closing true-up that makes sure the business is handed over with a normal level of short-term assets and liabilities, like receivables, payables, and deferred revenue. In SaaS, deferred revenue can feel counterintuitive because cash often arrives before revenue is recognized. Most owners do best by agreeing to a simple target based on historical averages and your billing model. Rejigg’s <a href="/owners/owners-guide/negotiate-a-deal" style="color: #1d4d05; font-weight: 600;">negotiation guide</a> explains how to handle this in plain English.
Earnouts pay you additional money later if the business hits agreed targets, often tied to ARR, retention, or revenue milestones. They show up when the buyer is concerned about churn, customer concentration, or founder dependence and wants proof after close. The main risk is getting measured on results you do not control, like the buyer changing pricing, support, or product investment. If you accept an earnout, push for tight definitions, reporting access, and clear operating control rules.
Not always. Many buyers do not require an SOC 2 report, especially in SMB-focused SaaS, but they will expect a security story that matches your customer base and your contracts. If you sell to enterprise or regulated customers, weak security practices can shrink the buyer pool or change terms. A practical security packet with access control, incident history, and current controls often goes a long way. Rejigg’s buyer vetting and digital NDAs help you share sensitive materials safely.
Buyers commonly ask for a production access summary, the process for granting and removing access, incident history, and recent security review or pen test summaries. They also often ask how you handle secrets, credentials, and logging. If you have completed customer security questionnaires, those can be helpful because they show what you have already committed to in writing. Keep the packet factual and release it through a secure data room after NDAs are signed.
Buyers usually split usage-based revenue into a predictable base and a variable layer. They look at how often customers exceed their commits, whether overages cause churn, and whether your pricing stays ahead of your real cost drivers like compute, data egress, and third-party API calls. If usage revenue is lumpy or concentrated in a few heavy accounts, buyers tend to underwrite conservatively or ask for protections. A simple usage forecast and a feature-to-cost map make valuation discussions faster.
You can run a serious process without spraying customer names and contracts to strangers. Start with an anonymized customer list and a renewal schedule, then share named contracts only after the buyer is vetted and under an NDA. Rejigg supports this workflow. Buyers are pre-vetted, NDAs are signed digitally, and you control exactly who sees sensitive files in the data room and when.
Problem contracts usually have obligations that do not show up in your headline metrics. Common examples include easy termination rights, unusual refund language, strict service level penalties, data handling commitments you cannot meet, and side letters promising custom features or special support. Buyers care most when these terms sit inside a top customer. Pull your top contracts early and build a one-page exceptions list so nothing gets “discovered” in week six.
Taxes depend on deal structure, whether you sell assets or equity, and how the purchase price gets allocated across software, customer relationships, and goodwill. Earnouts also affect timing, which can change when you owe tax on proceeds. This is worth modeling early with a tax professional so you do not win on price and lose on after-tax outcome. Keep your financials and contracts organized so your advisors can move quickly once offers arrive.
Many founders do 4–12 weeks of active handoff, then a lighter advisory period, but the right answer depends on where you are still a bottleneck. If you personally handle renewal saves, release approvals, and security escalations, buyers will ask for more overlap. If you have already assigned owners and rehearsed handoffs, you can usually negotiate a shorter transition. The <a href="/owners/owners-guide/transitioning-after-the-sale" style="color: #1d4d05; font-weight: 600;">transition planning guide</a> helps you put the plan on paper.
Expect to share financial statements, a customer list and renewal schedule, ARR roll-forward support, key contracts, vendor and hosting cost summaries, and basic security and technical docs like an architecture overview and incident summaries. The goal is to answer the questions that affect price and structure without turning diligence into chaos. Rejigg includes a built-in secure data room so you can stage materials and control access instead of emailing attachments.
Look past the headline number and compare how each buyer shares retention and execution risk. Line up cash at close, seller financing, earnout triggers and definitions, any holdback or escrow, and working capital targets. Also ask what the buyer plans to do with customer success, support staffing, and infrastructure spend, because that can change retention after close. Rejigg’s deal tracking and offer comparison dashboard let you compare terms side-by-side so you can pick the offer that nets out best.
Start by getting your subscription numbers tied to your actual billing and your retention data organized. List on <a href="/" style="color: #1d4d05; font-weight: 600;">Rejigg</a> where buyers are actively looking for software companies. You'll have direct conversations, share materials securely, and negotiate terms. Most cloud software sales close in three to eight months.
Most cloud software businesses sell for 3 to 8 times their annual profit. A "multiple" just means how many years of profit a buyer is willing to pay upfront. Where you land depends on how many customers stay and expand, how low your cancellation rate is, and whether the business runs without you. Try <a href="/" style="color: #1d4d05; font-weight: 600;">Rejigg</a>'s <a href="/valuation" style="color: #1d4d05; font-weight: 600;">free valuation calculator</a> for a starting estimate.
Most deals close in three to eight months. Things move faster when your subscription numbers match your billing records and the business runs without you handling every issue. The biggest slowdowns come from buyers discovering inconsistencies in the numbers or technical surprises late in the process.
No. Brokers charge 5 to 10 percent of the sale price, which is hard to justify when you can manage the process yourself. <a href="/" style="color: #1d4d05; font-weight: 600;">Rejigg</a> gives you buyer vetting, secure document sharing, and offer comparison tools. You keep control of the process and more of your sale price. <a href="/owners/schedule-consultation-call" style="color: #1d4d05; font-weight: 600;">Schedule a free consultation</a> to see how it works.
Subscription revenue that renews predictably. Customers who stay and use more over time. Revenue spread across many accounts so no single customer is too important. And a team that can ship updates, handle support, and manage renewals without you. Buyers also look at your technology costs and whether your product is something customers use every day.
Customer cancellations (churn) are one of the most important numbers buyers look at. If more than 10 to 15 percent of your customers leave each year, it raises concerns. Buyers will want to understand why people cancel and whether the trend is improving. If your churn is low, that's a major strength. Show your numbers by year so buyers can see the full picture.
Yes. Buyers want to understand how your product is built and whether it will need significant investment after the sale. A simple one-page overview of your technology, how updates get released, and any known areas that need work builds confidence. You don't need perfect code. You just need to be honest about where things stand and have a team that can keep improving it.
At minimum: your total subscription revenue broken out by customer, how many customers renewed last year, how many cancelled, your hosting and technology costs, and your top 10 customers by revenue. Having these numbers tied to your actual billing records is the single most important thing you can do to speed up the process and protect your asking price.

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