Getting access to high-level executives like Salesforce CEO Marc Benioff may require an extreme level of persistence. Harry Stebbings emailed him 53 times before getting a response. The key was that each follow-up included a new, personalized P.S., demonstrating thoughtful commitment rather than automated spam.
Most sales are lost to inertia, not rejection. Implement a specific, escalating follow-up sequence (30 mins, 60 mins, next day) after sending an offer. This disciplined approach isn't pushy; it helps busy prospects make a decision while their interest is at its peak.
Instead of directly asking to meet with a senior executive, first propose a more tactical next step with your current contact. Then, position the executive meeting as a logical 'next, next step' contingent on the success of the first. This reduces pressure and makes the request feel less abrupt.
During a sales cycle with Seismic, the rep held back specific pain points gathered from end-users to use in a follow-up email with personalized micro-demos. Instead of sharing everything in the first call, this unexpected, high-value touchpoint changed the course of the deal by demonstrating deep understanding.
Salespeople mistakenly delay follow-ups to avoid being 'annoying,' but this kills momentum. Prospects don't track outreach attempts like salespeople do. A steady, frequent cadence isn't pushy; it demonstrates reliability and preparation, proving you won't quit on them.
When traditional outreach for a licensing deal failed, Dr. Holman had 80 patients send personal Christmas cards to the CEO of Boehringer Ingelheim. The highly personal, non-digital approach bypassed corporate handlers, landed directly on the CEO's desk, and secured a meeting within a week.
Adding a deeply personal postscript (P.S.) to cold emails, such as referencing the recipient's favorite whiskey, demonstrates genuine research and builds rapport. This simple tactic humanizes the outreach and can dramatically increase the likelihood of getting a response from a busy executive.
When a prospect doesn't respond, don't default to thinking they're ignoring you. Instead, assume they are extremely busy and your message was lost in the noise. This mindset encourages persistent, multi-channel follow-up rather than premature disqualification.
Salespeople often worry about being annoying during follow-up because they frame it as a transactional attempt to close a deal. To overcome this, reframe follow-up as an opportunity to build and enhance the relationship. By consistently providing value—sharing insights, making introductions, or offering resources—the interaction becomes helpful rather than pestering.
Effective follow-up isn't about nagging; it's about being a 'barnacle on a boat.' This means staying in contact persistently, not by asking for the sale, but by delivering value every time. This strategy keeps you top-of-mind, building trust so that when the customer is finally ready to buy, you are the logical choice.
When a proposal goes silent, avoid empty 'checking in' emails, which position you as a nuisance. Instead, every follow-up must deliver additional insights or value relevant to the prospect's business. This reframes you as a helpful peer and consultant, keeping the conversation alive without sounding desperate.