- 01
Interview your best customers
- Book 30–45 min calls with 10–15 of your best customers
- Ask what was happening in their business when they started looking
- Ask what triggered the search and why they picked you over alternatives
- Write down their exact words, objections and who else was in the decision
- 02
Map triggers, personas and differentiation
- Build a trigger catalog: funding, leadership change, expansion, missed targets, competitor moves
- Rank triggers by frequency, urgency and how fast those deals closed
- List the 3–5 differentiators that actually won deals, per persona
- Profile each persona: KPIs, daily struggles, what makes them look good to their boss
- 03
Turn insights into trigger hypotheses
- Pick 3–5 triggers ranked by frequency, urgency and fit
- Write each as a testable statement (e.g. Series B raised plus hiring sales ops means scaling pain)
- Share the triggers and customer language with marketing and customer success
- 04
Write messaging and plan your channels
- For each trigger and persona, write a hook, problem, insight, proof and one clear CTA
- Reuse customer language from the interviews, keep it conversational
- Decide which channels your personas actually use: email, LinkedIn, phone, video, direct mail
- Map 14–18 touches over 2–3 weeks, mixing hard asks and soft engagement
- 05
Build and research a tight account list
- Define ICP criteria: size, industry, growth stage, tech stack, geography
- Pick 50–100 matching accounts and tier them A, B and C
- Spend 10–15 min per account finding 2–3 live triggers (news, job posts, exec posts)
- Map the buying committee: economic buyer, champion, technical buyer, end users
- 06
Personalize and run the sequence
- A accounts get fully custom research and video, B get 2–3 custom lines, C get one
- Run the sequence: email, LinkedIn connect, engage, calls, Loom, breakup email
- Reply to every response within 2 hours and ask for referrals when it is the wrong person
- Move "not right now" replies into nurture and respect every opt-out
- 07
Review weekly and refine
- Track meetings booked, referrals received and constructive rejections
- Break response rates down by channel, trigger and persona
- Block 1 hour every Friday to review what worked and update templates
- Swap in a new hypothesis when one fails to convert after 50+ attempts
- 08
Scale with AI once it works
- Only add AI after the fundamentals convert consistently
- Use Clay, Apollo or Sales Navigator for list building, enrichment and trigger alerts
- Use a power dialer (Orum, ConnectAndSell) for follow-ups, not cold first touches
- Randomly review 10% of outreach to keep quality up as volume grows
Tools mentioned
- LinkedIn Sales Navigator
- Clay
- Apollo
- Prospeo
- Icypeas
- Surfe
- Orum
- ConnectAndSell
- Loom
- BuiltWith
- Crunchbase
- PitchBook
- Google News alerts
- G2
- Capterra