Booking and Leading Meetings that Win Enterprise Deals

Yulia Mihlin

Today’s buyers are busy and bombarded with outreach—so how do you stand apart from other sellers? Relevant messaging content and strategic processes are key to booking meetings, growing pipeline and impacting KPIs.

Today’s buyers are busy and bombarded with outreach—so how do you stand apart from other sellers? Relevant messaging content and strategic processes are key to booking meetings, growing pipeline and impacting KPIs.

To uncover best practices used by revenue leaders for booking and leading meetings that result in bigger, better deals, we gathered an expert panel featuring Halit Berisha, Director of Sales Development at Databook, Alex Jagiello, Global Director of Revenue Development at Clari, and Francis Barrett, Account Executive at Celonis.  

These sales development leaders discussed their top strategies for accelerating seller success in the enterprise space. They shared practical tactics for creating personalized outreach content that cuts through the noise, booking enterprise sales meetings that hold, and increasing the odds of pipeline creation—even during the busy holiday season.

Here are some of our panel’s leading insights.

Engage C-suite and senior contacts up front and throughout the sales cycle

Outreach messaging that resonates with senior decision-makers helps accelerate enterprise deals. Get relevant content from YouTube interviews, podcasts, webinars and conferences, and financial docs like annual reports, 10Ks, and quarterly earnings transcripts. Databook users can also craft personalized messaging within a framework that cites executive priorities and intent, addresses a pain point, connects a use case, and ends with a strong call to action. Remember, the C-suite is busy, so short and sweet messaging will increase response rates.

Get more tips for selling to the C-suite >>

Create personalization frameworks

Leaders can support these efforts by providing message creation guidelines for the sales team to ensure content resonates with contacts and to maximize productivity.

For example, spend five minutes researching a person or account, find five pieces of information to inform personalized outreach, and spend five minutes writing each custom email. 

Pro tip:

Use research to incorporate buyers’ own language in messaging and to state a compelling event right at the beginning of an outreach effort.

Take little steps to make big meetings stick

You got the meeting—so what can you do next to make sure the prospect shows up? Try leveraging a gap process of 3-5 days from contact to scheduled meeting to help ensure prospects show up (a gap process for post-meetings can increase hold rates and move prospects into qualified pipelines). 

Follow-up communications are also critical; send a summary message right after scheduling a meeting, share a piece of relevant content 72 hours prior to the meeting, and do a day-of confirmation. 

Pro tip:

Avoid scheduling enterprise sales meetings at risky times (i.e. Friday afternoons, month/quarter/fiscal ends, etc.). Additionally, get prospects to accept meeting invites live while on a call, and include the why/incentive on a meeting agenda in the invite.

Adjust your plays around holidays to keep the momentum going

While Q4 is the busiest time of the year, full of year-end challenges and holiday travel, it also creates unique opportunities to generate pipeline. Again, think about what’s relevant to prospects at this time. Are they approaching annual planning? Navigating budget concerns or dealing with excess budget? Consider how can your product/solution might help people drive value around these compelling seasonal events, and center your messaging here.

Pro tip:

Frontload outreach and meetings at the beginning of the month. Match the season with an upbeat, cheerful attitude, and show your willingness to work around busy schedules by asking for post-holiday meetings.

Leverage multi-threading

Involve multiple stakeholders in the sales process and align different use cases to different personas. One way to do this is to ask contacts to refer teammates or invite them to a scheduled meeting. Another is to use a “bottom-up” or “walk the halls” strategy that broadens outreach to include end-user personas who can validate POV research and offer fresh perspectives. 

Take a multichannel approach

With typically 6-7 decision-makers involved in the buying process, our experts say there’s no silver bullet when it comes to communication channels. You have to do it all: phone, email, LinkedIn, and so on. Leave out one critical channel, and you’re potentially leaving money on the table.

Consider tapping into lesser-used media, like video or voicemail, to bump up your other touches and set yourself apart from other reps. But our panelists agree that phone calls are always a must, with close to 50% of enterprise sales meetings coming from this channel. Francis Barrett of Celonis calls it the “money maker” and says everything else is complementary.

Do the omnichannel [outreach]. Get the touches in there. That's all icing on the cake. But you're going to get the cake from the phone.

Francis Barrett, Celonis Account Executive

Put your tech stack to work

Revenue leaders know the right tech tools can really make a difference when it comes to sales efficiencies. Solutions our panelists swear by include: the email assistance platform Lavender, the sales engagement platforms Groove and Salesloft, sales intelligence tools like Zoominfo, and SRM from Databook.

Want more practical strategies from our webinar participants? Click below to hear the full discussion. Then, come join the Strategic Sales Network to get even more tips from leading sellers and keep the conversation going.

Full Webinar: Booking and Leading Meetings That Win Enterprise Deals

About the Author
  • Yulia Mihlin

    Yulia is a self-driven marketing leader with 17 years of experience in building revenue-generating marketing programs from the ground up in Fortune 500 companies and startups. Her areas of expertise include account-based marketing, demand generation, product marketing, digital marketing, and sales enablement. She is experienced in partnering closely with sales, executives, and marketing peers to develop and execute integrated account-based marketing motions that accelerate business growth.

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