Selling a Sales Tools Business

Based on hundreds of real buyer-seller conversations we’ve helped happen on Rejigg, these are the diligence topics that decide Sales Tools deals: what drives churn, how stable the CRM and inbox integrations are, and whether “ARR” quietly depends on ongoing human help.

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What buyers ask and how to be ready

Each topic below comes from real buyer-seller conversations. Here's what they ask, what they're really evaluating, and how to prepare.

Retention

What actually causes churn in your product?

Buyers are separating churn you couldn’t control, like a budget freeze or the champion leaving, from churn caused by weak adoption. In Sales Tools, churn usually traces back to workflow friction: reps never build the habit, managers never look at the dashboard, or the CRM connection breaks, and nobody notices. They want proof you can spot those patterns early and reduce repeats.

How to prepare

  • Tag the last 10–20 cancels with a churn reason and note whether it was preventable
  • Document your first-30-day onboarding steps and the 2–3 places customers commonly stall
  • Track time-to-first-value by segment, like first meetings booked or CRM sync completed

Great Answer

In the last 12 months, churn was mostly champion change, incomplete team rollout, and CRM permission issues that blocked the sync. Accounts that don’t connect the CRM in the first two weeks cancel at a much higher rate, so we made CRM connection and manager dashboard setup day-one requirements. Those newer cohorts are retaining better, and we can show the before-and-after by start month.

Okay

Churn is usually adoption and leadership changes. We can talk through examples, but we haven’t tagged and reported it consistently.

Gives Pause

Churn is low, and it’s mostly pricing. Every customer is different, so it’s hard to say why they cancel.

How Rejigg helps: Rejigg’s built-in data room lets you share churn notes, retention exports, and onboarding docs in one place so buyers can follow the churn story with evidence. Learn more in the guide

Integrations

How sticky are your integrations, and who owns them?

For most Sales Tools, the CRM and inbox integrations drive daily trust in the product. Buyers are looking for stability and ownership: where the integration code lives, how changes get shipped, and how you find breakages before customers do. They also want to know whether the “integration” is a real, maintained app or a fragile setup that depends on manual steps and tribal knowledge.

How to prepare

  • List your top integrations and the percent of customers using each
  • Document ownership for each integration, where the code lives, and the release process
  • Show monitoring, alerting, and the support escalation path for integration failures

Great Answer

About 70% of customers use Salesforce and 25% use HubSpot, and we can break that down by plan and segment. The Salesforce package is maintained in-house, documented, and covered by automated checks that alert us when key API calls fail. Support has a clear escalation path, and we publish release notes when a platform change affects setup.

Okay

Most customers connect Salesforce or HubSpot, and it usually works. One engineer owns it and can fix issues when they come up.

Gives Pause

Integrations aren’t a big deal because we have Zapier. If something breaks, customers usually tell us.

How Rejigg helps: Rejigg helps you organize integration docs, app listings, monitoring screenshots, and support runbooks in a secure data room with staged buyer access. Learn more in the guide

Revenue Quality

Is your revenue really subscription, or is it disguised services?

Buyers want to know whether they’re buying software margins or a services-heavy delivery model that props up renewals. In Sales Tools, onboarding, CRM cleanup, deliverability help, sequence migration, and custom reporting can be real value. If renewals depend on that help, the buyer has to underwrite headcount, support load, and gross margin differently.

How to prepare

  • Split revenue into subscription, usage-based fees, onboarding, integration work, and ongoing managed services
  • Define what onboarding includes and the typical hours and timeline by customer segment
  • Show delivery cost per onboarding and per managed account, even if it’s an estimate

Great Answer

Last year, revenue was 82% subscription, 10% onboarding, and 8% optional managed services. Standard onboarding has a clear finish line: CRM connection, field mapping, and two manager dashboards live within 14 days. Renewals don’t require managed services, and we can show retention for customers with zero services compared to customers who bought add-ons.

Okay

We have onboarding and setup fees, and some customers need more help than others. It’s mostly subscription, but it’s not cleanly separated yet.

Gives Pause

It’s all recurring because customers pay every month, even though we do a lot of ongoing setup for them.

How Rejigg helps: Rejigg’s QuickBooks integration pulls clean revenue detail into your data room so buyers can see the subscription versus services split without back-and-forth spreadsheets. Learn more in the guide

Owner Dependence

If the founder disappeared for 60 days, what would stop shipping or break customer confidence?

Buyers are checking whether the business runs on repeatable team habits or on the founder stepping in to save the day. In Sales Tools, that risk shows up fast because you sit inside live sales workflows. A missed escalation, a broken integration, or a confusing release can turn into churn quickly.

How to prepare

  • Map who owns each revenue moment: lead gen, demos, pilots, security reviews, procurement, onboarding, renewals, and expansions.
  • Document ownership for roadmap decisions, release communication, and escalation handling
  • Have the team run the next step on five active deals or renewals without you

Great Answer

If I stepped away for 60 days, sales keeps moving because two people own demos and pilots, and customer success owns renewals and QBRs (Quarterly Business Reviews). Product decisions run through our product lead and a weekly triage using support volume, win-loss notes, and adoption data. I still handle two partner relationships, and we have a contact map and handoff plan for both.

Okay

The team can keep things moving, but I still get pulled into bigger deals, roadmap calls, and escalations.

Gives Pause

Nothing would change because the product is self-serve. Customers don’t need us, and I’m not involved day-to-day.

How Rejigg helps: Rejigg deal tracking keeps buyer conversations, transition promises, and key-person dependencies written down so the handoff plan is concrete. Learn more in the guide

Adoption Signals

What does ‘good adoption’ look like in your product, and how do you measure it?

In Sales Tools, retention usually follows habits: reps using the tool weekly and managers using it in coaching. Buyers want a small set of usage signals that reliably predict renewals. They also want to see that you act on weak adoption early, not after a cancellation notice shows up.

How to prepare

  • Pick 2–4 usage metrics that correlate with renewals, like weekly active reps and manager dashboard views
  • Share adoption by cohort and segment, with a focus on the first 14–30 days
  • Write a simple save playbook for what happens when adoption drops

Great Answer

We define good adoption as 60% of seats active weekly plus weekly manager dashboard usage. Accounts that hit both by day 30 renew at a much higher rate, and we can show the cohort curve. When adoption dips, customer success runs a two-week relaunch with manager training and workflow resets, and we track the save rate from those interventions.

Okay

We look at logins and general usage, and we know adoption matters, but we don’t have a tight set of renewal predictors.

Gives Pause

Customers like us, and support tickets are low, so adoption is fine. We don’t track usage in detail.

How Rejigg helps: Rejigg’s data room gives you one place to share usage exports and cohort views so buyers can validate adoption with numbers. Learn more in the guide

Platform Risk

How exposed are you to platform changes from Salesforce, HubSpot, Google, or Microsoft?

Sales Tools depend on CRMs and inbox providers, so policy changes and API shifts can create urgent engineering work and surprise churn. Buyers want a clear dependency map and evidence you detect breakage fast. They are listening for whether you find issues through monitoring, or through customer complaints.

How to prepare

  • Quantify the percent of customers tied to each platform and which features rely on each dependency
  • Document monitoring and alerting for API failures, token refresh issues, and permission errors
  • Share examples of past platform changes and how you communicated and shipped fixes

Great Answer

About three quarters of customers require Salesforce or HubSpot, and two core workflows depend on those APIs. We monitor key calls and permission failures, and we have a customer comms playbook that includes in-app banners and updated setup guides. When Google tightened sending rules, we updated defaults the same week, published guidance, saw support spike for two weeks, and then watched it normalize.

Okay

We depend on major platforms, and we keep up with changes as they happen. We can usually adapt quickly.

Gives Pause

Platform risk isn’t a concern. If Salesforce or Google changes something, we’ll deal with it then.

How Rejigg helps: Rejigg makes it easy to share a dependency map, incident write-ups, and platform-change playbooks during diligence without emailing sensitive documents. Learn more in the guide

Compliance

What’s your deliverability and compliance posture?

For outbound and email-adjacent Sales Tools, deliverability and compliance show up as retention, refunds, and reputational risk. Buyers want to know whether customer results come from sustainable practices or from pushing limits that get domains burned and accounts restricted. They are also checking whether you have clear guardrails in the product, not just advice in a help doc.

How to prepare

  • Document defaults for send volume, throttling, opt-outs, and spam complaint handling
  • Show how you monitor deliverability signals and how you intervene when customers push limits
  • Document consent and recording expectations for calling by geography

Great Answer

We set clear defaults for send volume, throttling, and opt-outs, and we monitor spam complaints and deliverability signals so problems don’t linger. Customers who push limits get a written warning and a remediation plan, and we will disable risky behavior if needed. For calling and recording, our onboarding covers region-by-region expectations, and we keep it updated.

Okay

We follow best practices and coach customers on deliverability. We haven’t had major issues, but the process isn’t very formal.

Gives Pause

Deliverability is the customer’s problem. We don’t control usage, and we don’t track spam complaints.

How Rejigg helps: Rejigg’s buyer vetting and digital NDAs let you share deliverability and compliance policies with serious buyers without broadcasting sensitive details. Learn more in the guide

Positioning

Do you win because of a niche, or because you’re cheaper than the suite?

Buyers are trying to understand whether you own a real workflow or whether you’re a feature that will get bundled away. Crowded Sales Tools categories are normal, so “competition exists” is not the issue. Value comes from a clear win pattern that matches real win-loss notes and retention by segment.

How to prepare

  • Pull your top 3 win reasons and top 3 loss reasons from real deals, with concrete examples
  • Write a short statement for who the product is for and what you will not build
  • Identify the best-retaining segment and tie it to a specific workflow you support end-to-end

Great Answer

We win with mid-market outbound teams because managers use our coaching workflows in weekly one-on-ones, and customers keep historical scorecards and reporting inside the product. We lose deals where security requires single sign-on and audit logs we don’t support yet, and we have that work scoped and scheduled. Our pricing shows up as reasonable, but the decision is driven by this coaching workflow being better than what the suite offers.

Okay

We usually win on ease of use and fast setup. We lose some deals to suite vendors and procurement, and we’re working on it.

Gives Pause

We’re basically the same as the big tools, just cheaper and more flexible.

How Rejigg helps: Rejigg lets you tell your niche story directly to buyers through your listing and buyer conversations, without a broker sanding it down into generic SaaS language. Learn more in the guide

Growth Channels

Where does new ARR actually come from: product-led, outbound, partners, or founder network?

Buyers want to know whether growth is repeatable and hireable, or whether it depends on you personally. In Sales Tools, they also look for channel fragility: outbound that dies when deliverability slips, partnerships that are friendly but non-committal, or an “inbound” story that is really one conference or one influencer. Clean channel proof reduces discounting during diligence.

How to prepare

  • Break down the last 12 months of new ARR by channel and show the month-by-month trend
  • Write down the one or two channels you would scale next and what makes them work today
  • Document operational dependencies by channel, like deliverability ownership or partner referral terms

Great Answer

In the last 12 months, new ARR was 45% outbound, 35% partners, and 20% inbound content. Outbound performs because we have a tight ideal customer profile and a deliverability playbook new hires follow, and we can show conversion by stage. Partners are three agencies with clear referral fees and steady lead flow, and none drive more than 15% of pipeline.

Okay

We get customers from a mix of outbound and referrals. It’s working, but we don’t have a clean channel breakdown with trends.

Gives Pause

Mostly word of mouth and my network. We haven’t tracked where deals come from.

How Rejigg helps: Rejigg’s deal tracking helps you keep a clean record of lead source, buyer conversations, and offers so your growth story holds up under questions. Learn more in the guide

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Questions Sales Tools Owners Ask Us

A Sales Tools company is usually priced off profit, then adjusted up or down based on what a buyer thinks is durable. Retention quality, stability of Salesforce and HubSpot integrations, and how much ongoing human work is required to keep accounts renewing tend to move the number the most. You can get a fast starting point with Rejigg’s free valuation calculator, then tighten it up by sharing churn drivers and your subscription versus services split.

No. Brokers often charge 5–10% of the sale price for coordination and packaging work you can run yourself with the right tools and buyer access. Rejigg gives you pre-vetted buyers, digital NDAs, direct messaging, a secure data room, and a dashboard to compare offers side-by-side. Start with the preparation guide so your materials are ready before the first call.

Split revenue the way a buyer will model it: subscription, usage-based fees, onboarding, integration work, and ongoing managed services. For Sales Tools, the key diligence question is whether services are optional acceleration or required for renewals, like deliverability hand-holding or ongoing CRM reporting tweaks. Bring typical hours per onboarding by segment and retention for customers who bought zero services. Rejigg’s secure data room makes it easy to share invoice examples and the “what’s included” policy cleanly.

Net revenue retention measures what happens to last year’s customer revenue after churn and expansions are combined into one number. Sales Tools buyers care because it reflects real in-account behavior: seat rollouts, manager adoption, and whether customers consolidate tools. If expansion comes from seats that never went live, buyers will question durability. Use Rejigg’s data room to share cohort retention plus notes on what drove expansions so the percentage has a clear story behind it.

Many Sales Tools deals use a mix of cash at close, seller financing, and an earnout tied to future performance. SBA loans can work for some software acquisitions, but lenders usually want clean books, predictable cash flow, and low customer concentration. Before you negotiate, model realistic payments and debt coverage using the SBA loan calculator so you understand what a financed buyer can actually pay.

Many deals close in a few months, but Sales Tools timelines often stretch when diligence gets stuck on CRM integrations, security reviews, or whether “subscription revenue” is really services in disguise. Speed comes from having churn notes, dependency maps, onboarding runbooks, and a clean revenue split ready on day one. Rejigg keeps NDAs, buyer messaging, scheduling, and diligence docs in one place so you do not lose weeks chasing email threads.

Buyers will ask for the basics, like financial statements, customer lists, and contracts, plus Sales Tools specifics: integration ownership and architecture, security posture, churn and expansion by cohort, onboarding and support runbooks, and a clear breakdown of onboarding and managed services revenue. Many will also request usage exports because adoption predicts renewals in this category. Rejigg’s due diligence checklist and built-in data room help you package it without scattering files.

A working capital adjustment is a closing true-up so the business hands over with a normal level of short-term assets and liabilities, like accounts payable and accrued expenses. In SaaS-style Sales Tools, deferred revenue from annual prepay contracts can make this confusing because cash and revenue timing do not line up. Bring a clear billing and renewal schedule so you can spot surprises early. Rejigg’s deal tracking helps you keep working-capital terms visible across competing offers.

An earnout can help close a valuation gap, but it also leaves part of your payout tied to how the business runs after you hand it off. In Sales Tools, metrics can get impacted by platform changes, deliverability shifts, or a new go-to-market motion that you do not control. If you consider one, keep the metric simple, measurable, and tied to data both sides can verify. Use Rejigg’s deal negotiation guide and offer comparison to weigh structure versus price.

Seller financing means you take part of the purchase price over time, usually as a note paid monthly or quarterly. It’s common in smaller Sales Tools deals because it helps the buyer fund the purchase and signals you believe the retention and integration story will hold. The trade-off is credit risk and post-close execution risk. If you do it, get clear payment terms and protections if payments are missed. Rejigg’s offer comparison helps you weigh structure versus headline price across bids.

Buyers look at contract terms and the real renewal motion: annual versus monthly, auto-renew language, discounting habits, and who owns renewals today. In Sales Tools, renewals can be champion-led, so a clean contract does not always prevent churn when leadership changes. Organizing agreements, renewal dates, and key account notes reduces last-minute surprises in diligence. Rejigg’s data room lets you share contracts with controlled access and stage what buyers see as they get serious.

Sales Tools often touch sensitive data, like emails, call recordings, CRM notes, and pipeline fields, so buyers dig into the security items that slow down sales cycles. Common asks include single sign-on, role-based permissions, audit logs, data retention controls, and how access to inboxes and recordings is managed internally. You do not need every enterprise checkbox, but you do need consistent answers and clear policies. Store your standard responses in Rejigg’s data room so diligence stays organized.

Share information in layers. Start with a high-level overview, then only release sensitive items, like customer lists, pricing, churn notes, and integration details, once a buyer is qualified and under NDA. Rejigg supports this directly: buyers are pre-vetted, NDAs are signed digitally, and you can grant staged access inside the secure data room. That keeps competitors and tire-kickers from learning how your product and go-to-market really work.

Taxes depend on your entity and deal structure, but the practical point is simple: structure can change what you keep after taxes by a meaningful amount. Buyers often push for structures that help their write-offs, while sellers often prefer structures that improve personal tax treatment. Bring an accountant in early enough to compare offers on net proceeds, not headline price. Rejigg’s offer comparison dashboard helps you keep the structure details straight while advisors weigh in.

A common transition is a few months, with the highest leverage in the first 30–90 days. That window usually covers renewals in flight, integration ownership, security questionnaires, and escalation paths that keep customers calm. If you personally drive sales or product calls, buyers may ask for longer, but you can keep it bounded with a written scope and calendar. Rejigg’s transition planning guide helps you define who owns what.

A non-compete is an agreement that limits you from starting or joining a directly competing Sales Tools business for a set period after the sale. Buyers often ask for one because the space is crowded, and relationships with customers, partners, and key hires can matter. Scope varies a lot by niche and market, so keep it specific to what the buyer actually needs protected. Capture the terms early using Rejigg’s deal negotiation guide.

Assume integrations will get deep diligence and package the proof upfront. Share a list of integrations, the percent of customers on each, who maintains them, how changes are tested and shipped, and how you detect failures. Also include a short history of recent Salesforce, HubSpot, Google, or Microsoft changes and how fast you responded. When buyers see ownership and monitoring, they spend less time pricing “unknown churn” into the deal. Rejigg’s data room lets you share this the minute NDAs are signed.