Mastering the Art of Navigating Gatekeepers and Decision-Makers

In SaaS sales, one of the most difficult challenges is navigating the intricate network of gatekeepers to reach the actual decision-makers. These gatekeepers are often the unsung guardians of their bosses’ time and attention, and they can either pave the way to a successful meeting or block access entirely (which is more common). Here are tactical tips and strategies to help you connect with more buyers and turn gatekeepers into allies.

Understanding the Role of Gatekeepers

Gatekeepers, such as executive assistants and receptionists, are employed to manage the influx of information and requests directed at decision-makers. They filter out irrelevant or less important calls and emails, ensuring that their bosses’ time is spent efficiently. If you have ever had an interview, there is usually a person who you speak with for just a few minutes to “screen” you as a prospective hire and make sure you should move through to the next step of the interview process. Think of a gatekeeper in this context. Recognizing the importance of their role is the first step in navigating this challenge.

Strategies for Navigating Gatekeepers

1. Research and Preparation

Before reaching out, conduct thorough research on the company and the decision-maker. Understand their business initiatives, challenges, and industry trends that are most common to their business. This preparation will help you tailor your approach and demonstrate you understnad their business and worthy of time of the decision maker. For public companies, check out our article on how to leverage the 10-K to do research here.

2. Respect and Professionalism

Always treat gatekeepers with respect and professionalism. Acknowledge their position and the value they bring to their organization. A respectful approach can turn gatekeepers into advocates for your cause. I have done things to get on their good size such as dropping off coffee, flowers, giving them tickets to a game, or some relevant swag to get on their good side. Most times, I didn’t ask for the favor to get time with the decision maker until we have established a little bit of rapour.

3. Clear and Concise Communication

When you contact a gatekeeper, be clear and concise about your intentions. You will need to clearly explain how your solution addresses a specific problem or top-level initiative that is relevant to their company. Avoid jargon and be direct about the purpose of your meeting request. The more you can speak in their terms, or company jargon, the better your chances will be.

4. Timing Your Contact

Timing can be everything. Avoid calling first thing in the morning or right before the end of the day. Mid-morning or mid-afternoon, when things are less hectic, might increase your chances of success. If someone comes to my house unannounced and the dogs are barking, kids are going crazy, I am way less likely to want to sit and chat. To contrast, if I am out in public sitting at a fun bar or restaurant, it’s much easier to strike up an easy conversation with someone. Find times of less chaos, and use that to your advantage. Thursday’s, and Friday’s have worked well for me in the past, or emailing Sunday night will have much less competition.

5. Leveraging Referrals

If possible, leverage referrals from within the company or industry. Being able to name-drop a mutual connection can provide instant credibility and may help you bypass the gatekeeper altogether. You can find similar customers who your company has done business with and share the value/outcomes your organization drove. If you can find someone within the prospect who worked at another customer even better.

6. Persistence and Patience

Persistence is key, but it must be balanced with patience. If you’re asked to call back or send information, do so promptly and professionally. Follow-up is important, but avoid becoming a nuisance. You can continue to send webinar or events your company is hosting, or relevant articles you think the decision maker will find interesting. A mentor of mine used to say “be like a commercial that keeps playing over and over in their head”.

7. Asking for Help

Sometimes, simply asking the gatekeeper for help can be effective. Phrase your request in a way that enlists their aid in solving a problem or improving a process within their company. Something like this: “Hey Sara, I am wondering i fyou can help me out? I know your organization is really trying to drive costs down in your contact center. We actually saved a large competitor of yours 30% on average handle time, which equates to $2,000,000 annually. Who would be the best person to talk to about this?”

8. Utilizing Voicemail Strategically

If you reach a voicemail, leave a message that is compelling and succinct. Make sure to mention the value proposition and express your eagerness to discuss how you can help address their challenges. Pair this, with persistence and continue to follow up via email, Linkedin, and dropping by in person, and you will get a meeting. I would leave a voicemail at 7AM every Monday morning for a CIO I was trying to speak with for 3 months straight before I got a response. Those who quit will never get the meeting, but those who are persistent eventually do.

Conclusion

Navigating gatekeepers requires a blend of research, respect, and strategic communication. By understanding their role and approaching them as valuable members of the organization, you can turn potential obstacles into opportunities for connection. Remember, the gatekeeper you impress today could be the decision-maker of tomorrow