Starting Where You Are

• How many add-on acquisitions has your team completed in the last 24 months? Options: None, 1, 2-3, 4-6, 7+
• Tell me about the most recent close, focusing on timeline, key handoffs, and one surprise your team encountered.
• Name the person who led day-to-day integration and the function they represented. Options: CEO, CFO, Head of Ops, Head of Product, Head of Sales, Other
• List the three metrics your team watches in the first 90 days after close. Options: Revenue run-rate, Gross margin, Customer retention, Employee retention, Support tickets, Other
• Share a concrete example of an acquisition that exceeded expectations and what changed because of it.
• Estimate how much management time, in hours per week, acquisitions typically consume for your leadership team in the first three months. Options: <5 hours, 5-10 hours, 10-20 hours, 20-40 hours, 40+ hours

What Breaks First When Integration Stresses Operations

• If an add-on reduced your customer retention by 3 percentage points this quarter, would you still push the integration forward? Options: Yes, with mitigation, Only if short-term pain is compensated, No, we would pause integration, Unsure
• Describe which operational process—billing, order fulfillment, support—would feel the impact first and why. Options: Billing, Order fulfillment, Customer support, Logistics, Other
• When a recent integration caused a spike in support tickets, how long did elevated tickets remain above baseline? Options: <1 week, 1-2 weeks, 2-4 weeks, 1-3 months, Still elevated
• Who on your operations team is authorized to pause customer-impacting changes if metrics deteriorate? Options: Head of Ops, COO, CEO, CRO, Other
• Choose the scenarios that most worry you during integration. Options: Loss of customers, Departure of key staff, Data migration failures, Contract breaches, Unexpected legal exposure, Other
• Which single operational constraint, if unresolved, would make you stop pursuing an acquisition right now?

Are We Aligned on Why This Acquisition Matters

• If the deal met revenue targets but required two quarters of margin compression, would leadership accept that trade-off? Options: Yes, Only with offsetting savings, No, Undecided
• Outline the top two strategic objectives from your 3-year plan this acquisition must support. Options: Customer expansion, New geography, New product capability, Cost synergies, Scale distribution, Other
• Who will be accountable to the board for tracking acquisition ROI, and what cadence of reporting do they already produce? Options: Monthly P&L, Quarterly board deck, Ad hoc updates, Other
• List the three KPIs that must move within 12 months for you to call the acquisition successful. Options: EBITDA, Net retention, Gross margin, Active customers, Churn rate, Other
• Which metric would make you walk away immediately if the target could not meet it in the first year?
• Rate your appetite for short-term disruption from this acquisition Options: Zero tolerance, Low tolerance, Moderate tolerance, High tolerance

The Price, The Deal, The Boundaries

• Suppose the seller required a price 15% above your target cap, would you withdraw of pursue with adjusted terms? Options: Withdraw, Pursue with reduced scope, Pursue with additional approvals, Unsure
• Identify the purchase agreement clauses your CFO considers non-negotiable. Options: Indemnities, Escrow amounts, Working capital adjustments, Non-competes, Earnouts, Other
• Name the retention and incentive mechanisms you typically deploy to keep acquired leaders and critical staff. Options: Equity rollover, Cash retention bonus, Performance earnout, Extended benefits, Other
• Estimate the valuation multiple range you would consider for targets of your usual size. Options: <4x, 4-6x, 6-8x, 8-10x, 10x+
• Choose which deal boundaries are deal breakers for you. Options: Geography limits, Material litigation, Large customer concentration, Negative working capital, Regulatory encumbrances
• Specify the approver who must clear any above-capacity price increase for the deal to proceed immediately. Options: CFO, CEO, Investment Committee, Board Chair, Other

Integration Risks That Keep You Up at Night

• Would replacing a core system to enable integration be acceptable, and under what budget conditions? Options: Acceptable within budget X, Acceptable with phased approach, Not acceptable, Undecided
• Provide the parts of your tech stack that must remain untouched during migration.
• Identify who owns API access and the credentials needed to migrate customer and billing data.
• On a scale from 'not ready' to 'clean and deduplicated', how mature are your customer data hygiene practices? Options: Not ready, Some cleanup required, Mostly clean, Clean and deduplicated
• Are there regulatory or contractual approvals that could block transfer of customer contracts? Options: Yes - customer consent needed, Yes - regulator sign-off needed, No, Unsure
• Declare the technical constraint that, if unresolved within 30 days of LOI, would terminate the project.

The Alternatives You Are Weighing

• Assuming your current approach were delivering the plan, what would have to be true for you to keep it rather than partner externally?
• Provide the internal teams that have proposed executing add-ons without outside support. Options: Corporate Development, Portfolio Ops, Business Unit Leaders, Finance, Other
• Share the incumbent vendors or advisors you currently use for deals of this size.
• Would staying with your incumbent partner require changes for you to meet the timeline and targets we discussed? Options: Yes, process changes, Yes, budget changes, No, Unsure
• What single condition would cause you to reject external help and proceed with an internal-only approach?
• Select the alternative solutions you are actively evaluating. Options: Do nothing / organic growth, Internal M&A team, Boutique M&A advisor, Strategic partner, Other PE-backed platform
• How much confidence do you have in each alternative's ability to preserve customer relationships? Options: High, Moderate, Low, No confidence

Can You Deliver On Day One — Readiness and Constraints

• Assume access to named systems and data is delayed by 10 business days after signature, can your integration timeline remain intact? Options: Yes, Only with schedule changes, No, Unsure
• Identify the systems that must be reachable with API or SFTP to complete a typical migration.
• Who will supply credentials and where will they be stored during migration? Options: Internal IT, Third-party vendor, Shared vault, Other
• Estimate the headcount and skill mix you can assign to integrations over the next six months. Options: <1 FTE, 1-3 FTEs, 4-6 FTEs, 7+ FTEs
• Are there existing vendor contracts that limit how you transfer data or customers? Options: Yes - restrict transfer, Yes - require notice/consent, No, Unsure
• Which single resourcing gap, if not filled within two weeks of LOI, would prevent you from starting integration?
• Select the compliance or regulatory gates that could delay close. Options: Customer consent, Data residency sign-off, Regulatory approval, Contract novation, Other
• Describe your emergency rollback process for the first 30 days after launch.

Close the Loop — Decision Drivers and Next Steps

• If a pilot proves the uplift you expect, what remains that could stop you from signing the deal within a week?
• Which approvals, signatures, or board votes must occur before you can commit? Options: CEO sign-off, CFO sign-off, Investment Committee, Board approval, Other
• Name the internal champion who will drive week-to-week decisions through closing.
• What is your target closing window from LOI to signed agreement? Options: <2 weeks, 2-4 weeks, 1-3 months, 3+ months, Undecided
• Which single remaining question, if answered positively today, would let us move to a mutual commit this week?
• Select how soon you'd like a follow-up planning workshop. Options: Immediately (this week), Within 2 weeks, Within 1 month, Unsure

• Integration Strategy Session

• Confirm the current state and its cost
• You confirm the demonstrated scenarios remove the main sources of integration disruption you described.
• Provide three representative target profiles with last 12 months of revenue, contribution margin, and headcount by function.
• You agree on the success metrics and go/no-go criteria that will be used to advance a target to Acquisition Scope.
• Walk through two realistic target scenarios and P&L impact
• Deliver a scenario-modeled P&L and integration risk register for the selected pilot target within five business days.
• Map the integration playbook to your operating model
• You commit to one pilot target to move into scoped diligence with named owners and timelines.
• Confirm the approval authority and maximum investment threshold required to proceed to Acquisition Scope.
• Validate success metrics and go/no-go criteria
• Forced validation, confirm this maps to what you meant

• Integration Strategy Session
• Integration Strategy Deck
• Integration Strategy Solution Brief

• meeting
• slides
• document

• Source and Outreach to Target Sellers
• Deliver Screened Target Pipeline
• Execute Financial and Operational Due Diligence
• Negotiate and Finalize Purchase Terms
• Draft and Execute Letter of Intent
• Manage Transaction Closing and Funds Transfer
• Migrate Acquired Company CRM Records
• Consolidate Accounting and Reporting Systems
• Onboard Key Employees and Transfer Benefits
• Execute First-100-Day Integration Playbook
• Run Customer Transition and Contract Notifications
• Integrate IT Systems and Data Migrations

Source and Outreach to Target Sellers

• Do you have an existing target criteria list (for example revenue range, geography, NAICS codes) to drive outreach? Options: Yes, No
• How many broker or intermediary relationships should be included in active outreach per quarter? Options: 0-5, 6-15, 16-50, 50+
• Which outreach channels should be prioritized (for example broker CRM introductions, direct-owner email, trade show contacts)? Options: Broker/Intermediary outreach, Direct-owner outreach, Industry events/trade shows, Advisor referrals, Digital outreach
• Who will be the named owner for inbound outreach responses and lead qualification (provide name and contact role)?
• When do you expect the first outbound campaign to launch and what target list size should it include (for example month and number of targets)? Options: Within 30 days, 30-60 days, 60-90 days, Custom date

Deliver Screened Target Pipeline

• What is the primary screening metric you require on each target profile (for example trailing twelve months revenue, gross margin, recurring revenue percent)? Options: Revenue, EBITDA / adjusted EBITDA, Recurring revenue %, Customer concentration, Custom metric
• Specify the minimum revenue and EBITDA ranges we should filter on for the pipeline (for example $1-5M revenue, $250-500K EBITDA).
• Provide the scorecard fields you want in each target profile (for example revenue growth, tech stack, top 10 customers percentage).
• List the red flags that should exclude a target from the screened pipeline (for example active litigation, >30% customer concentration, unresolved regulatory findings).
• Are there any geographic or regulatory jurisdictions we must exclude from the pipeline (for example non-qualified countries or states with compliance issues)? Options: No exclusions, Exclude non-domestic entities, Exclude specified states/jurisdictions, Custom list

Execute Financial and Operational Due Diligence

• Will you require a forensic quality of earnings (QoE) report or a standard adjusted EBITDA analysis for targets? Options: Forensic QoE, Standard adjusted EBITDA, Both, TBD
• Estimate the depth of vendor contract review needed (for example top 20 supplier contracts, all master services agreements, change-of-control clauses). Options: Top 10 suppliers, Top 20 suppliers, All suppliers, Custom scope
• Confirm which financial periods should be covered by diligence (for example last 12 months, fiscal year-end trailing twelve months, three-year trend). Options: Last 12 months, Fiscal year TTM, 3-year trend, Custom range
• Identify the operational systems we must access for diligence (for example your source CRM exports, order management database, inventory SKU master).
• Describe the cost synergy tests we should run on payroll, overlapping SG&A, and shared procurement categories (for example vendor repricing potential, headcount overlap count).

Negotiate and Finalize Purchase Terms

• Which valuation assumptions should guide term negotiation (for example target EBITDA multiple range, working capital peg, earnout hurdles)?
• What is the maximum cash consideration you are willing to approve before requiring investment committee escalation?
• Specify the preferred deal structures to propose (for example asset purchase, stock purchase, membership interest sale). Options: Asset purchase, Stock purchase, Membership interest, Hybrid/Other
• Provide the target indemnity cap and survival period ranges you want to negotiate (for example cap = 100% of purchase price, survival = 12-24 months).
• Who on your team is authorized to approve negotiated term sheets up to defined thresholds (provide name and approval limit)?

Draft and Execute Letter of Intent

• Do you require the LOI to include exclusivity and standstill clauses? Options: Yes - exclusivity required, No exclusivity required, Need discussion
• List the conditions precedent that must appear in the LOI (for example satisfactory due diligence, regulatory approvals, third-party consents).
• When should the exclusivity period in the LOI start and what duration (in days) is acceptable? Options: Start at LOI signature, Start at signing of confidentiality agreement, Custom start date
• What signatures and witness requirements do you expect on the executed LOI (for example authorized signer, notary, witness on schedules)? Options: Authorized signer only, Authorized signer + witness, Notary required, Other
• Identify any third-party notification templates you want attached to the LOI (for example broker fee letter, landlord consent notice).

Manage Transaction Closing and Funds Transfer

• What escrow or holdback mechanics should be included in the purchase agreement and escrow instructions (for example escrow amount, release conditions)?
• Describe the wire and bank account verification process you require for final funds transfer (for example template wire instructions, KYC checklist, bank confirmation steps).
• Confirm which closing deliverables you require in escrow (for example executed purchase agreement, officers' certificates, resignations, consents).
• What evidence will validate that funds transfer and closing are complete (for example cleared wire confirmation, released escrow statement)?
• Who will be the authorized signer and provide the bank-sourced signature verification letter at closing (provide name and title)?

Migrate Acquired Company CRM Records

• How many contact, account, deal, and activity records must be migrated from the source CRM export (provide counts by object if available)? Options: Less than 5,000 total, 5,000-25,000, 25,000-100,000, More than 100,000
• Indicate the record types that require historical activity migration (for example past 24 months of calls, invoices, support tickets). Options: Contacts, Accounts, Opportunities/Deals, Activities/Notes, Support tickets
• What mapping rules should be applied between source CRM fields and the integration endpoint (for example account ID, custom tag fields, lead source)?
• What acceptance criteria will confirm the CRM migration is complete (for example 99% account match rate, zero orphaned deals, reconciled activity samples)?
• Choose the de-duplication strategy you prefer for CRM records (for example match on email+company, fuzzy name match, manual review threshold). Options: Exact email+company match, Fuzzy name + company, Manual review above threshold, Custom rule set

Consolidate Accounting and Reporting Systems

• Indicate the target chart of accounts file or mapping example you will provide for general ledger mapping.
• What reconciliation tolerance thresholds should apply to accounts payable / accounts receivable roll-forwards (for example <0.5% variance, <$5,000 absolute)? Options: <0.5%, <1%, <2%, Custom $ threshold
• Explain the deferred revenue and subscription ID mapping required to align recurring revenue in consolidated reporting.
• What evidence will validate consolidated reporting is accepted by finance (for example closing pack, trial balance match, variance analysis signed off)?
• Name the person who will provide historical P&L and balance sheet source files and point contacts for GL mapping (include file path or SFTP user if available).

Onboard Key Employees and Transfer Benefits

• Are you able to provide an employee census file export (for example payroll ID, hire date, compensation, benefits election) for the acquired company? Options: Yes - complete census available, Partial census available, No census available
• What notice or offer letter templates should be used for new employment contracts and benefits enrollment?
• Name the payroll provider category and benefits carrier types that require cutover coordination (for example payroll provider export, medical carrier enrollment files, 401(k) vendor).
• How will you handle accrued vacation and final payroll runs for transferring employees (for example cutoff payroll period and payout rules)? Options: Payout accrued on final payroll, Leave accrual transferred to new system, Custom approach - describe
• Detail the benefits enrollment artifacts that must be migrated (for example plan IDs, employee elections file, COBRA notices).

Execute First-100-Day Integration Playbook

• What are the critical day-one operations we must preserve (for example billing runs, customer support SLAs, fulfillment cutoffs)?
• Define the 30/60/90 milestones that must be in the playbook with owners (for example CRM cutover day+30, pricing harmonization day+60).
• Please list the individuals assigned to handle customer escalations and the 24-hour response process during integration (name and role).
• Explain the contingency steps if the CRM cutover misses its data migration window (for example fallback to dual-write, manual order entry procedures).
• What communication templates should be included for customer-facing emails and service desk scripts during the first 100 days? Options: Customer email templates, Support script templates, Billing notification templates, All of the above

Run Customer Transition and Contract Notifications

• Detail the customer contract types that require assignment or consent notifications (for example material statements of work, master service agreements, reseller agreements).
• When should customers receive transition notices relative to close (for example immediate, 7 days after close, at first billing)? Options: Immediate (at close), Within 7 days after close, At first billing cycle, Custom timing
• Define the customer segments that should receive white-glove outreach versus standard email notification (for example top 10 accounts, regulated customers).
• How will you handle contract assignment that triggers change-of-control consent requests for strategic customers (for example pre-notify, request consent, escrow solution)?
• What customer-facing SLA or billing changes should be included in notification templates (for example invoice remittance changes, new support hours)?

Integrate IT Systems and Data Migrations

• Are API documentation and service accounts available for the systems to be integrated (provide SFTP/API endpoint list)? Options: Yes - docs and accounts available, Partial - some endpoints available, No - access not available yet
• Select the data flows that must be real-time versus batch (for example order creation, inventory sync, customer status). Options: Real-time order creation, Batch inventory sync, Real-time customer status, Custom flows
• What authentication and rate-limit expectations exist for the APIs to be used (for example OAuth tokens, 1000 requests per minute)?
• What rollback plan will you accept if a data migration introduces duplicate invoices or inventory mismatches (for example freeze, reconciliation script, reverse batch)? Options: Reverse batch + reconciliation, Freeze new writes + manual reconcile, Dual-write fallback, Custom plan
• Estimate the monitoring and alert thresholds to be configured post-migration (for example failed sync rate >1%, unmatched SKUs >0.1%).

• Purchase Agreement
• Disclosure Schedules
• Escrow & Holdback Agreement
• Transition Services Agreement (TSA)
• Key Employee Retention Agreements
• Closing Conditions & Deliverables Checklist
• Approval & Signatory Matrix
• Governance & Post-Closing Oversight Agreement
• Tax Allocation & Contingent Liability Agreement
• Regulatory Filings & Consents Plan

• Go-live Health Check (Weeks 1-4)
• First Outcomes Measurement Review (Weeks 4-10)
• Acceptance Gate — 90-Day Outcome Decision
• Quarterly Value Realization Review

• Product/ops to update the shared enhancement request channel and notify stakeholders of planned delivery windows.
• Validate and certify the financial data sources feeding the acceptance gate report.
• Restate acceptance criteria and required signatory
• Produce a documented acceptance decision for the acquisition integration with the named signatory recorded.
• Create a binding remediation plan with owners and dates for any conditional or failed criteria.
• Confirm the incumbent system decommissioning or retention approach and the archival status of legacy data.
• Publish the signed acceptance record and distribute to governance stakeholders.
• Open remediation tickets for any conditional items with owners, milestones, and review dates.
• Execute incumbent system contract closeout or convert to read-only and archive data per the agreed schedule.
• KPI dashboard review versus Acquisition Scope targets
• Confirm whether realized EBITDA contribution and customer satisfaction are sustained against the Acquisition Scope run-rate.
• Maintain a prioritized backlog of enhancement requests with owners and delivery windows.
• Agree the monitoring cadence and data owners for the next quarter.
• Owner to close the top 3 backlog items impacting retention or CSAT within the agreed quarter.
• Finance to publish the quarterly EBITDA reconciliation versus Acquisition Scope projections.
• Re-confirm scope, success criteria, and owners
• All deployment completion items are confirmed done or have named owners and resolution dates.
• Top 3 operational blockers are triaged with owners and committed resolution dates.
• Agreement on the data sources and cadence for the first outcomes measurement.
• Publish the deployment completion checklist annotated with owners and resolution dates.
• Deliver the adoption and system-health logs to the review team within 5 business days.
• Create escalation path documentation and distribute to named owners.
• Present first-period results against Acquisition Scope targets
• Determine whether consolidated EBITDA and 90-day retention are trending toward the Acquisition Scope targets or require remediation.
• Name owners and delivery dates for the top corrective actions needed before the acceptance gate.
• Confirm data validation steps so the acceptance gate can rely on the presented figures.
• Produce a variance pack showing line-item drivers for EBITDA delta and retention cohort behavior.
• Implement the agreed retention initiatives for acquired accounts and report weekly adoption metrics.
• Present final outcome data against each criterion
• Realized synergies validation
• Deployment and migration validation
• Variance analysis and root-cause diagnosis
• Document pass/fail and capture formal acceptance decision
• Early adoption signals and usage patterns
• Open issues and enhancement request backlog
• Operational blockers impacting financials or retention
• Blocker triage and immediate remediation plan
• Agree corrective actions, owners, and dates
• Operational risk and escalation review
• Agree remediation plan for any failed or conditional criteria
• Next steps and short-term checkpoints
• Incumbent system wind-down and data archival check
• Next quarter monitoring plan and checkpoints