🚀 How to nail cold calling?

Sep 30: Dinner with Box’s Product Leader and Crunchbase’s former CPO (Apply Now)

Join a curated, small gathering for early-stage founders to discuss pricing strategies with Megh Gautam, Box’s Head of Product (Apps) and Crunchbase’s former CPO. Drawing on his leadership experience scaling revenues from 0 to 100M+ and teams from 0 to 100+ across household names like Crunchbase, Twilio and Dropbox, Megh will share insights on:

• Picking the pricing model that matches your costs

• ​Common traps when pricing your product

• ​How to know if customers are willing to pay more

Preference will be given to technical seed founders with strong early traction.

3 tactics to nail cold calling

💬 Answer “Why You, Why Now”

• Start with answering two questions about the specific person you’re calling:

  • Why might this person care about what your startup does?

  • Why should they care right now?

• Build an infrastructure to document "why you, why you now" personalization for:

  • Every industry you want to sell into (e.g. financial services, logistics, e-commerce, retail, healthcare, tech) 

  • Every persona within each industry (e.g. developers, architects, platform engineers, engineering managers, SREs, CTOs) 

• Spend at least 10-20 mins pulling up the prospect's LinkedIn profile to craft a thesis of why this person may care, and find something specific that signals you did research:

  • Recommendation someone wrote for them 

  • Projects they mentioned

  • Career transitions

  • Speaking engagements

🗣️ Practice until perfect

• Internalized at least one customer story per industry to the point where pressure and nerves can't shake you loose

  • You should be able to walk through the entire story of who the company is, what challenges they were facing, how your product helped 

• Spend about 8 to 10 hours per week on cold call practice

  • Practice your opening, know the customer story you are going to reference, and be able to explain the pain without rambling

  • Do one-on-one role plays and timed "why you, why now" exercises with various LinkedIn profiles

  • Aim to build a personalized opening in 20 seconds; start from 2 minutes then compress to 90 seconds, then 60, then 20

🎯 Be extremely intentional

• Start with a custom, manually-researched email and a call two days later

  • Personalize every touch, and make sure nothing is automated spray-and-pray

  • Aim for about 3 touchpoints between email and phone over a 10-day period, and about 8 touches over 30 days

• Have prospects see your brand elsewhere before the cold outreach:

  • Run coordinated marketing campaigns (e.g. custom landing pages for tier-one targets, personalized messaging paid ads etc) 

  • Show case studies from their specific industry, the exact challenges solved, and the business outcomes that resulted

2 traps to avoid

🚨 Not having a strong foundation of data

• Do not skip on running multiple data providers (e.g. LeadIQ, Lusha, Apollo, ZoomInfo etc.) 

• For any given prospect, have at least 3 independent chances to find a verified cell phone number and/or a verified email address 

• The redundancy is expensive but necessary when you’re doing high touch and low volume; you don’t want to accidentally call the spouse of a prospect

🚨 Stopping at the first dead-end

• Don’t just move on if the first contact information of a prospect is dead; reach out to other known numbers and emails as well

• You already did the hard work of researching the prospect, building your "why you," and getting them into a cadence

• One data provider might have missed it, but other providers may provide additional options

1 tool to leverage

📖 Best practice on cold calling

• Connect rate on cold calls (the percentage of dials where someone actually answers) is 5-7%; aim for a 40-50% conversion rate on those connections to meetings booked

• Have every cold outreach follow this 5-step structure:

  • Why you: Lead with something specific about prospects background or company that earns the right the to their time

  • Why now: Anchor to a timely trigger (e.g. funding, hiring, leadership change, recent announcements, etc)

  • Discovery: Ask a discovery question. Learn about their current stage, pain, or workflow. Qualify and build credibility

  • Close: Ask to book the meeting. Flip back to a relevant value proposition, strong customer proof, and ask to book a follow up session

  • Objection: Handle or redirect objections. Revalidate timing and try again or exit gracefully. 

  • A good cold call should only run about two minutes.

Bonus: 1 trend to spark startup ideas

📖 Trends and insights from Intuit & Poshmark’s Board Member

• Video recording and takeaway notes from our recent dinner with Deborah Liu, Intuit & Poshmark’s Board Member and former CEO at Ancestry and VP at Meta.

• We covered everything from why teams shipping twice as fast on AI are still seeing flat results, to the tactic used to build trust and close enterprise deals.