GTM Agency ×

Caddi GTM Playbook

GTM Audit & Playbook. ICP matrix and signal-based outbound plays, built for Caddi.
Prepared for Jason
$1.53M
Revenue generated for AirOps
100/mo
Meetings booked for Peoplelogic
500+
SaaS companies scaled

Previously ran growth for 500+ SaaS companies through their product launches. Our team has also worked with companies backed by

a16z Y Combinator Sequoia Lightspeed Techstars Wing Boldstart
Booked, qualified demos within 45 days or you don't pay

This playbook maps Caddi's ideal customer profile across account, prospect, and persona dimensions, then lays out 5 signal-based outbound plays. Each play fires on a specific buying signal so your outreach lands the moment a prospect is most likely to act.

01

Account Level

DimensionQualifiedPrioritization
GeographyUnited States, Canada, United KingdomPrioritize US-based firms with 20+ back-office staff
Employee Count20 to 500 employeesSweet spot is 30 to 200; firms large enough to feel ops pain but lean enough to lack a dedicated automation team
Industry / VerticalLaw firms, RIAs, accounting firms, private equity ops, insurance carriersPrioritize law firms (Am Law 200 and below) and RIAs with AUM over $500M
Key Qualifying SignalActive use of 2+ legal or financial ops tools from Caddi's integration set (Clio, NetDocuments, iManage, Orion, Addepar, Black Diamond, Filevine, Litify)Firms running 3+ disconnected back-office tools are highest priority, indicating manual handoff workflows and automation-ready complexity
Tech StackMicrosoft 365 or Google Workspace plus at least one vertical SaaS (Clio, NetDocuments, iManage, Salesforce, Filevine, Orion, Addepar, eMoney, Black Diamond)Microsoft 365 plus NetDocuments or iManage signals a law firm; Orion or Addepar plus Salesforce signals an RIA
Revenue / FundingLaw firms: $2M to $50M annual revenue; RIAs: $500M to $10B AUM; funded startups in legal or fintech opsFirms that recently raised or merged are under pressure to scale ops without headcount
Intent SignalsJob postings for legal ops coordinator, operations manager, or RIA operations specialist; G2 or Capterra reviews of Zapier, Make, or UiPath; attendance at ILTACON or Future Proof conferenceHiring for manual ops roles signals unmet automation demand; competitor review activity signals active evaluation
02

Prospect Level

DimensionQualifiedPrioritization
SeniorityC-Suite, VP, Director, Senior ManagerPrioritize COO and Director of Operations as primary; CTO and Managing Partner as secondary
Primary TitlesCOO, Chief Operating Officer, Director of Operations, Legal Operations Manager, RIA Operations Director, Firm AdministratorCOO and Firm Administrator own the budget and feel the daily workflow pain directly
Secondary InfluencersCTO, IT Director, Managing Partner, Practice Group Leader, Chief of StaffIT Director controls integration approvals; Managing Partner approves spend at smaller firms
LinkedIn Keywordslegal operations, law firm automation, RIA operations, practice management, workflow automation, back office efficiency, legal tech, fintech ops, process improvement, NetDocuments, Clio, iManage, Orion, AddeparProfiles mentioning specific vertical software (Clio, NetDocuments, Orion) confirm the tech stack overlap and role relevance
03

Persona Matrix

PersonaLevelKPIsRelated ChallengesIntent SignalsRelated Benefits
Law Firm COO / Firm AdministratorC-Suite / DirectorHours saved per attorney, cost per matter, staff utilization rate, client intake cycle timeManual new matter setup delays onboarding, conflict checks require dedicated headcount, document filing backlogs slow case progressPosting for legal ops hire, attending ILTACON, reviewing automation tools on G2, LinkedIn posts about law firm efficiencyAutomates new matter setup, conflict checks, and document filing so the firm takes on more matters without adding ops headcount
RIA Chief Operating OfficerC-SuiteCost per client account, advisor-to-ops staff ratio, onboarding cycle time, compliance audit readinessAdvisor count growing faster than ops capacity, manual data entry across Orion and Salesforce, compliance documentation is error-pronePosting for operations coordinator, attending Future Proof conference, evaluating Zapier or Power AutomateTriples advisor capacity without expanding ops by automating account onboarding, reporting workflows, and client communication routing
Legal Operations ManagerManager / DirectorAutomation coverage rate, SLA compliance on intake, document accuracy rate, time to first response on client emailsDependent on IT to build any integration, existing RPA tools require technical maintenance, no audit trail for automated actionsSearching for no-code automation tools, posting LinkedIn content about legal ops, active on ILTA community forumsBuilds and deploys automations by screensharing a process once, with full run history and audit logging requiring no IT involvement
IT Director / CTO (Law or RIA)Director / VPUptime SLA compliance, security audit pass rate, integration sprawl reduction, time to provision new toolsShadow IT risk from staff using ungoverned AI tools, integration maintenance burden, compliance with data handling requirementsEvaluating SSO and SAML vendors, reviewing SOC 2 compliance pages, posting about AI governanceCentralized MFA management, action-level audit logging, SAML SSO, and SCIM provisioning reduce governance risk while enabling ops automation
Managing Partner / Practice Group LeaderC-Suite / VPRevenue per attorney, client acquisition cost, realization rate, staff retentionLosing associates to burnout from repetitive filing and data entry, inability to scale intake without hiring, competitors onboarding clients fasterReading legal business publications, attending ABA or ILTACON events, LinkedIn posts about law firm growthAutomates drudgery so attorneys focus on billable work, reduces time-to-onboard for new clients, and delivers a concrete hours-saved number to justify AI investment
Signal-Based Plays

Outbound Play Breakdown

PLAY 01 · Legal Ops Hiring Signal Play

Signal-BasedTrigger: A law firm or RIA posts a job opening for a Legal Operations Manager, Operations Coordinator, or RIA Operations Specialist, signaling unmet workflow automation demand and active ops pain

What We Do

We target COOs and Firm Administrators at firms actively hiring for manual ops roles, the clearest signal that back-office workflows are overwhelming existing staff. Outreach connects their hiring pain directly to Caddi's 904 hours saved per month proof point.

Scrape job postings
Scrape job postings
Monitor LinkedIn jobs
Monitor LinkedIn jobs
Aggregate signals
Aggregate signals
Listen, De-anon & Enrich
Issue tracker · activity · headcount
Enrich firm data
Verify tech stack
Find decision maker
Identify Buying Committee
COOFirm AdministratorManaging Partner
Email
01Day 1: Hiring pain opener referencing open role02Day 3: 904 hrs/mo proof point with peer firm example03Day 7: Workflow-specific use case (new matter setup or client intake)04Day 12: Soft close with demo offer
OutcomeMeeting Booked
PLAY 02 · ILTACON Conference Attendee Play

Signal-BasedTrigger: A law firm operations leader or legal tech decision maker registers for or is confirmed attending ILTACON, signaling active investment in legal technology evaluation

What We Do

We scrape confirmed ILTACON attendee lists and LinkedIn event check-ins to identify COOs, IT Directors, and Firm Administrators at law firms. Outreach is timed to pre-conference, at-conference, and post-conference windows when evaluation intent is highest.

Signal Sources
Scrape event attendees
Monitor LinkedIn event
Cross-reference firm list
Enrich Account
Enrich attendee profiles
Find firm tech stack
Locate contact emails
Qualified ICP Filter
Am Law 200 or boutique firmCOO or IT Director titleActive Clio, iManage, or NetDocuments user
Email
01Pre-conference: Reference ILTACON and shared agenda02At-conference: Invite to Caddi booth or 15-min meeting03Post-conference: Follow-up with use case matching their firm type
LinkedIn
01Connect request with event context02Message referencing a session topic and Caddi use case
OutcomeMeeting Booked
PLAY 03 · Competitor Stack Detection Play

Signal-BasedTrigger: A law firm or RIA is detected running Zapier, Make, Power Automate, or UiPath alongside a Caddi-compatible legal or financial ops tool, signaling an active but underperforming automation stack

What We Do

We identify firms already running generic automation tools on top of Clio, NetDocuments, Orion, or Addepar, meaning they have automation intent but are stitching it together manually. Outreach positions Caddi as purpose-built for professional services versus generic no-code tools.

Signal Sources
Detect competitor tools
Cross-match vertical SaaS
Build account list
Enrich firmographics
Enrich firmographics
Identify ops leaders
Identify ops leaders
Verify emails
Verify emails
Identify Buying Committee
COODirector of OperationsIT Director
Email
01Day 1: Acknowledge their current stack and its known limitations for legal workflows02Day 4: Contrast Caddi screenshare setup vs. Zapier connector-building03Day 9: Specific use case for their vertical with hours-saved data04Day 14: Demo invite with no-pressure framing
OutcomeMeeting Booked
PLAY 04 · Champion Job Change Play

Signal-BasedTrigger: A COO, Director of Operations, or Firm Administrator who previously used or evaluated Caddi starts a new role at a different law firm or RIA, creating a warm re-entry opportunity

What We Do

We track job changes of former Caddi champions and ops leaders at peer firms using UserGems, then reach out within the first 30 days of their new role when they are actively auditing processes and have budget influence. Outreach leverages their prior familiarity and the pain they already know.

Signal Sources
Track champion job changes
Monitor LinkedIn updates
Flag new role alerts
ICP Filter
New role within last 30 daysNew employer is law firm or RIANew firm has 20+ employees
Enrich & Score
Match · enrich · score
Enrich new employer
Verify new firm tech stack
Confirm contact details
Identify Buying Committee
COOFirm AdministratorManaging Partner
Email
01Day 1: Congrats on new role, reference shared history or peer firm results02Day 5: Connect new firm's likely workflow pain to Caddi use cases03Day 10: Offer a fast 20-min workflow audit call
LinkedIn
01Congrats message on new role02Follow-up referencing a relevant workflow win
OutcomeMeeting Booked
PLAY 05 · Funding and Merger Signal Play

Signal-BasedTrigger: A law firm announces a lateral hire wave or merger, or an RIA announces a new funding round or acquisition, signaling rapid headcount and client growth that will strain existing back-office workflows

What We Do

We monitor press releases, Crunchbase funding rounds, and legal industry news for law firm mergers and RIA acquisitions, then reach out to COOs and operations leaders within days of the announcement. Outreach frames Caddi as the way to scale operations without a proportional ops headcount increase.

Signal Sources
Monitor funding rounds
Track merger announcements
Aggregate firm news
Qualified Filter
Announced event within last 21 daysLaw firm or RIA vertical50+ combined employee count post-event
Enrich
Enrich firm and contacts
Find ops decision makers
Verify contact emails
Buying Committee
COOChief of StaffDirector of Operations
Email
01Day 1: Reference the specific merger or funding event and its ops implications02Day 5: Frame ops headcount math: Caddi customer tripled advisor count without expanding ops team03Day 10: Offer a 20-min workflow audit scoped to integration complexity post-merger04Day 16: Final follow-up with peer firm proof point
OutcomeMeeting Booked
How the engagement works

What you get

Demos in 45 Days

You'll have qualified demos booked in your calendar within 45 days: infrastructure, sequences, and live campaigns installed for you.

No Retainer

You don't pay a retainer. Everything we build belongs to you from day one: data, playbooks, and infrastructure.

You Don't Pay If It Doesn't Work

If by day 45 you aren't seeing qualified demos booked in your calendar, we keep working completely for free until you do.

Put these plays into production

Ready to build your revenue engine?

We build and install a fully automated, signal-based outbound system, outbound, ads, and content, in a 45-day sprint. No retainer, and you own everything. Demos booked in 45 days or we work free until they are.

Leo Bosuener  ·  Founder, GTM Agency