Before you start: what you need
- Admin access to your CRM (Salesforce or HubSpot) for the OAuth connection
- A list of your first 25 pilot accounts with renewal dates and ARR — from your CRM or a spreadsheet
- The sending email address for renewal outreach (can be a shared mailbox or individual CSM address)
- One CSM who will own the approval queue during the pilot
Day 1: CRM connection and data mapping
Connect your CRM and map the fields that matter
Renewal360 connects to Salesforce and HubSpot via OAuth — no API keys required. The connection takes about 10 minutes. The field mapping takes longer and is worth doing carefully, because it determines the quality of the data your health scores and AI drafts will be built on.
Map these fields as a minimum: renewal date (or contract end date), ARR (or MRR), primary contact name and email, account owner, company name, and industry. Optional but recommended: last login date, NPS score, open support ticket count, and account tier label if you have one in your CRM already.
- OAuth connection to CRM completed
- Renewal date field mapped and confirmed correct on 5 test accounts
- ARR / contract value field mapped
- Primary contact and email fields mapped
- Optional enrichment fields mapped where available
Day 2: Account import and initial health scoring
Import your 25 pilot accounts and configure health scoring signals
Import your pilot accounts either directly from the CRM sync or via CSV if you want to control the initial set precisely. 25 accounts is the recommended starting size — enough to get meaningful data, small enough to manage carefully during the pilot.
Configure the five health scoring signals with default weights as a starting point. You'll calibrate these after your first renewal cycle, so getting them perfect now isn't the goal. The goal is having a working model that produces differentiated scores across your 25 accounts — not a flat distribution where everything scores 70.
- 25 pilot accounts imported
- Renewal dates visible and correct for all accounts
- 5 health scoring signals configured (usage trend, engagement, support, payment, NPS)
- Initial health scores visible — confirm at least 3 segments exist (healthy / at-risk / escalated)
Day 3: Segment setup and tier assignment
Define your ARR tiers and assign each account
Create your ARR-based segments — typically 2–3 tiers for a 25-account pilot. Name them clearly: Enterprise, Mid-market, SMB, or whatever labels match your internal language. Set the ARR thresholds for each tier. Assign each of your 25 accounts to the correct segment — the CRM sync should auto-assign most of them based on the ARR field you mapped on Day 1.
The segment assignment determines which sequence each account enters. Spend 10 minutes reviewing the auto-assignments and correcting any that are wrong before moving to Day 4.
- 2–3 segments created with ARR thresholds defined
- All 25 accounts assigned to a segment
- Manual overrides applied for any accounts that don't fit the ARR-based assignment
- Escalation threshold (health score minimum) set per segment
Day 4: Sequence design and email templates
Build your first two sequences — healthy track and at-risk track
Start with one segment — your mid-market or primary tier — and build two sequence tracks: healthy and at-risk. The healthy track is a standard 3-touch sequence (T-90, T-60, T-30). The at-risk track adds frequency and an escalation branch.
For each sequence step, write a brief email brief — 2–3 sentences describing what the email should communicate and any specific account context to reference. The AI uses this brief to generate the personalised draft when the sequence activates on a specific account. You don't write the final email here — you write the instruction set that the AI uses to write it.
- Healthy track: 3 touchpoints mapped at T-90, T-60, T-30
- At-risk track: 4–5 touchpoints with compressed timing and escalation branch
- Email brief written for each sequence step
- Branching logic set: reply detection → pause; health drop → escalate
The most common setup mistake at Day 4
Teams spend too long writing the email briefs and trying to perfect the copy before any real account data is flowing. The AI draft quality improves significantly once it has actual account context to work with — usage data, industry, recent support interactions. Write adequate briefs on Day 4, then refine them after you see the first AI drafts on Day 7. Iteration beats perfection at this stage.
Day 5: Approval queue and inbox connection
Connect the sending inbox and configure the CSM approval queue
Connect the sending email account via OAuth (Gmail or Outlook). This enables both outbound sending and the IMAP reply detection that pauses sequences when a customer responds. Test reply detection by sending a test sequence to an internal email address and replying — confirm the sequence pauses before Day 7.
Assign the approval queue to the CSM who will own the pilot. Set their notification preference — the default is Slack notification when new drafts are waiting. If Slack isn't connected, email notification works equally well.
- Sending inbox connected via OAuth
- Reply detection tested and confirmed working
- Approval queue assigned to pilot CSM
- Notification preference configured (Slack or email)
- Daily digest enabled for leadership if applicable
Day 6: Dashboard configuration and alert thresholds
Set up the renewal pipeline dashboard and health alerts
Configure the renewal pipeline dashboard with your three primary views: ARR renewing by month (next 90 days), accounts by health tier, and per-CSM pipeline summary. For the pilot, the "per-CSM" view will just show one CSM — but building the view correctly now means it scales without reconfiguration.
Set alert thresholds: which health score drop should trigger a Slack alert to the account owner? The default is a drop of 15+ points in 7 days. Adjust based on your scoring scale. Set a separate threshold for executive alerts — health score below 40 on any account over $50K ARR is a reasonable starting point.
- ARR-by-month view showing next 90 days of renewals
- Health tier distribution visible across all 25 accounts
- Account-level alerts configured for health score drops
- Executive alert threshold set for high-value at-risk accounts
Day 7: First accounts go live
Activate sequences and review your first AI drafts
Activate sequences on all 25 accounts. For accounts with renewal dates within 90 days, the first touchpoint will be queued for immediate AI draft generation. The approval queue will start populating within a few minutes — your CSM will see the first drafts ready for review.
Review the first 3–5 drafts together with the pilot CSM. Note anything that looks off in the personalisation — this is usually a field mapping issue from Day 1 rather than a model quality problem. Fix any mapping issues and regenerate. The goal by end of Day 7 is at least one approved and sent email.
- Sequences activated on all 25 accounts
- First AI drafts visible in approval queue
- At least one draft reviewed, edited if needed, and sent
- Reply detection confirmed working on a live account
- Dashboard showing correct status for all active accounts
Week 2: Calibrate and expand
By the end of day 7, the core system is live. Week 2 is calibration: reviewing the AI draft quality across account types, adjusting health scoring weights if the distribution looks flat, and expanding to additional account segments once the primary tier is running smoothly.
Most teams expand from 25 to their full account base within 3–4 weeks. The pilot period exists to validate that the setup is correct before scaling — not because the system needs 3 weeks to work, but because catching a misconfigured field on 25 accounts is a 10-minute fix, and catching it on 200 accounts requires more work. Full plan details and account limits are on the pricing page. If you'd like a broader overview of what the system does before starting setup, the How It Works page covers the full workflow from CRM sync to approved email — the same seven days described here, shown as a product flow.
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