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Enterprise sellers should prioritize building a relationship with the executive assistant (EA). The EA controls the executive's calendar, agenda, and priorities, making them a powerful gatekeeper and strategic partner for gaining access, not just an obstacle to overcome.
To secure an initial meeting, have the founder reach out to the C-level executive while an Account Executive (AE) simultaneously contacts their direct report (N-1). This dual-pronged approach increases the chances of engagement and can create internal buzz about your company.
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.
Your current contact is not an obstacle; they are a potential ally who can help you navigate their organization. By framing the C-suite conversation as something you are doing *for* them and their company's benefit, you can turn a potential gatekeeper into an invaluable internal champion who facilitates access.
A leader's role in removing sales friction includes leveraging their own executive network. When a seller cannot get access to a high-level decision-maker like a CFO, the sales leader should broker a peer-to-peer meeting (e.g., their CFO to the prospect's CFO) to establish credibility and accelerate the deal.
Instead of a standard sales pitch, propose a strategic meeting between your executive and theirs (e.g., your CDAIO meets their CIO). CC your executive's EA to add credibility. This reframes the request from a low-value sales call to a high-value networking opportunity for their boss.
For initial outreach, contact the CEO or COO with a humble request for feedback, not a hard sales pitch. These executives will often delegate the call to the appropriate team lead. This creates a warm intro to the right person, who is now more receptive because the request came from their boss.
Lower-level contacts often block access to leadership for two main reasons: fear you will waste their boss's time (hurting their credibility) or take their power. Proactively address these fears by positioning the C-suite meeting as an informative session that will make *them* look good, not a sales pitch that undermines them.
Before pitching the C-suite, gain crucial context by speaking with influencers and champions at lower levels within the organization. This internal research provides far more relevant insight than any online search, ensuring your executive pitch is meaningful.
Rather than approaching executives first, prospect the individual contributors who will actually use your solution. By creating internal champions at the user level, you generate a 'gravitational pull' that brings you into executive conversations with pre-built support, making decision-makers more receptive to your message.
Top decision-makers are often inaccessible. Instead of direct outreach, use a "multi-threading" approach by building relationships with 5-10 other people in their organization. These internal advocates can provide intelligence and eventually carry your message and credibility to the ultimate decision-maker, bypassing their usual defenses. This lengthens the sales cycle but is essential for large deals.