How to Win Over the C-Suite and Drive Faster & Larger Deals

How to Win Over the C-Suite and Drive Faster & Larger Deals


Engaging decision-makers who influence buying decisions is crucial for companies selling to enterprise customers. However, convincing the C-suite, one of the most desired audiences for B2B marketers can be a daunting task. They are unlikely to take time away from the office unless they are convinced it will be worth their while. Nonetheless, winning over the C-suite is highly rewarding, as it can lead to larger deals and faster sales than you ever thought possible.


In this article, I will be sharing tactics from my recently published book, The Ultimate B2B Marketing List: 200+ Innovative Tactics You Need to Try. While I did not dedicate a chapter specifically to CxO Marketing, I have captured tactics on how to engage the executive audience across different sections of the book, including the top B2B marketing trends, getting to know your dream buyers, crafting killer content, keeping customers coming back for more and other tactics to try.


This article is divided into two parts: Building the Foundation and Activation. The first part talks about the groundwork for a successful C-suite engagement strategy while the second part we’ll explore tactics for activating your strategy and getting the coveted attention of the C-suite.

Building the Foundation


Building a solid foundation is absolutely important for any successful CxO Marketing strategy. To get it right, several key questions need to be addressed. For example, what are the objectives and goals of the CxO Marketing strategy? Are we aiming to drive deeper account penetration, change market perception, or target new accounts? It’s important to clearly define the goals and align them with the overall business objectives.


Another key consideration is determining the selection criteria for the accounts and executives that will be included in the CxO Marketing program. It is good to be selective and choose accounts and their executives that have high potential to generate great ROI. This will require careful research and analysis to identify the targets for the best results.


In this foundation stage, I have included four parts: The CxO Marketing Approach, Account and Executive Selection, Metrics for Success, and the Account and Executive Dossier.

The CxO Marketing Approach


Once we have established the objectives and expected ROI of the CxO Marketing strategy, it’s important to determine whether the approach will be one-to-one, one-to-few, or one-to-many. This decision will impact the target account selection, content creation, and targeting strategy.

Account & Executive Selection

Winning over the C-suite requires a strategic approach that begins with identifying the right accounts and executives to target. Rather than pursuing a high-volume game, it’s better to focus on carefully selected accounts and do it very well.


Collaborate closely with the sales team to create a focused accounts list and determine the appropriate CxO Marketing approach as discussed above.


Identify who ultimately selects these accounts – sales, marketing, or senior leadership – and the method for selecting them. After the accounts have been selected, build the CxO list. According to Gartner, the typical business-buying group includes between six and 10 decision-makers. Therefore, it is wise to consider all executives who benefit or can benefit from your offering, not just the typical top authority and budget holder.


Note that executives trust and depend heavily on their team of subordinates and managers to research and evaluate technology investments. Hence, it is always important to target the broader buying committee as well. And do not neglect the gatekeeper: the executive assistants.


Finally, it’s essential to verify the location, size, industry, and any other aspects that could show a tendency to purchase the target account. Gather information on rank, influence patterns, and organizational dynamics.

Metrics for Success


To ensure the success of a CxO Strategy, determine the duration of the program and the metrics used to measure success. Goals could include improving reputation, building relationships, increasing sales pipeline, accelerating deal close, and of course, revenue.


As the C-Suite is generally concerned with long-term success, it pays off to develop a long-term cultivation strategy with a proactive and systematic plan for all key relationships. This plan should be coherent and substantive, with quarterly touchpoints that include surprising elements to keep CxOs engaged.


Ideally, there should be a robust dashboard that consolidates all data points to track results. This will provide stakeholders with the ability to measure the performance of all campaigns, generate reports, and uncover trends and opportunities. It is important to measure progress on a real-time or near-real-time basis so that tweaks and improvements can be made over time. Accountability, execution, and refinement over time are key to success.

The Account and Executive Dossier


Gaining and deepening account knowledge is an indispensable part to achieve successful CxO Marketing. This involves collecting information and insights from various sources to create detailed account plans and dossiers.


The main goal is to develop executive dossiers that summarize and organizes the research into a live document to help you gain a full understanding of the target accounts and their executives.


The account dossiers should provide valuable findings and recommendations by analyzing various factors, such as the socioeconomic environment, industry trends (good or bad), market positioning, growth potential, plans, opportunities, and challenges.


Meanwhile, the executive dossiers should include important information about the target CxOs, such as their name, title, personality style, interests, bio, associations, boards, important clients/prospects, priorities, areas of focus, direct reports, trusted advisors, their manager/board, common connections and more. It’s essential to do detailed research to gain insights about the target personas’ priorities, pain points, business concerns, and industry trends and how the offering acutely maps to them.


This information will ensure we gain their attention and effectively engage them. Research can be done by reading business journals, and press articles, following them on social media, and reviewing filings and quarterly earnings reports, annual reports among other sources.



Once the groundwork is completed, we move to the activation stage, where we put all the foundational work into action. The idea is to build messaging & assets, campaigns, and engagements that will win the heart of the C-Suite.

Messaging & Assets


As a CxO marketer, we know that executives are inundated with information; but we also know that they are seeking valuable insights and understanding. The messaging and assets should therefore acutely align with their top priorities as identified in the research phase. This could include industry trends, relevant breaking news, and peer benchmarks. To stand out, the content must be tailored specifically to the C-suite audience, addressing their greatest business challenges with intriguing, surprising, or useful ideas. By focusing on their top priorities and creating relevant, credible, and engaging content, trust and goodwill are built.


It goes without saying to focus on insights and understanding, rather than a sales pitch. You can weave your relevant offering to the CxO priorities and share strong evidence in the form of stories, case studies, white papers, statistics, testimonials, and so on.


Personalization is key, so it’s important to develop a content strategy for each decision-maker and influencer that is tailored to their specific areas.


Start early and stay strong in the approach, remaining visible and relevant at each stage of the buyer’s journey. Newsletters, white papers, eBooks, videos, webinars, and other relevant content can be used to keep the targets engaged and interested.

Engagement Strategies and Campaign Orchestration


Run an Integrated Multi-Channel Strategy to Gain Attention and Engage CxOs:


To effectively engage with C-level executives, it’s essential to employ a multi-channel strategy. With numerous channels available, such as email, executive events, digital ads, social media, and webinars, there’s no one-size-fits-all solution. While email can be effective with a great subject line and relevant content, the most successful campaigns integrate multiple channels to reach various decision-makers.


To maximize impact, as discussed, ensure that the content is valuable and tailored to the target audience’s priorities and areas of interest. Establish systematic touchpoints, including a mix of business, social, and soft touchpoints, to build a lasting impression. Consider using direct mail, such as a handwritten congratulatory card or sending a book of interest, to cut through the noise and differentiate from competitors.


To make the campaign truly compelling, incorporate unexpected elements into the engagement program such as sending a tailored study comparing the recipient’s firm with its competitors or other personalized assets. By utilizing a combination of channels and creative elements, you can gain the attention of CxOs and start meaningful conversations.


Make Use of Executive Entry Points


After identifying a significant opportunity, establishing direct connections between your company and the target company can be highly beneficial. These C-to-C connections can help build trust and facilitate collaboration.


For existing customers, it’s essential to make use of entry points that provide executive access. Timing is crucial here; for instance, it’s wise to reach out to senior executives during the period after the contract has been signed but before the project begins. This provides an opportunity to align goals and ensure that everyone is on the same page.


Similarly, midway through a project, sharing mid-term results with senior executives can be an effective way to keep them engaged and informed. Finally, when the project is complete, follow-up discussions with executives can help cement the relationship and open doors for future opportunities.


Digital dominates


In the world of B2B marketing, digital dominates. Although traditional face-to-face contact is still powerful, the majority of the buyer’s journey is now conducted online. As stated in my book on page 6 “In B2B, 57% -70% of the buying decisions are made before buyers even talk to a company and their sales team”.


Pre-purchase research and vendor evaluation is done on digital platforms such as online search, blogs, webinars, podcasts, and social media. Buyers’ teams freely share articles, research reports, and executive guides, while also combing through potential vendors’ websites, searching for key players on Google, and going to review sites. To be where prospects are looking, digital must be a big part of the strategy to get in front of today’s time-starved executive suite.


Forrester reports that the number of buying interactions increased from 17 to 27, with mainly online touchpoints. This can provide important clues to inform content plans, ad campaigns, and sales strategies. By understanding what information CxOs search for, what pages they visit on the website, and what content they download, new content and marketing approaches that better address their needs can be effectively shaped and a new model for an ABM (Account Based Marketing) can be built accordingly.


There’s No Substitute for Face-to-Face Interaction


In the last part of this article, I would like to talk about the importance of face-to-face interaction with the C-Suite, and for marketing this means events. Yet we all know, that getting them to attend an event and take time off their day is extremely challenging.


I have organized CxO events since 2003, and here are my top 10 tips to make your events irresistible to these busy leaders :


Connect them with their Peers


C-level executives prefer learning from their peers. To engage them, connect them with peers and experts who can share relevant insights and make a strong case for value. At events, a speaker roster with peer leaders who can share case studies and lessons learned can be a powerful strategy. Aim to invite external experts such as analysts, authors, industry leaders, and influencers whom participants identify as thought-provoking and inspirational.


Leverage Your Senior Executives


Enlisting your own C-suite to help host a peer conversation is a great way to draw in others and build credibility. For example, if you’re hoping to convene CIOs at your next event, get your CIO to serve as the draw by sharing their story as part of the program. Commitment from your executive team reinforces your focus on value-added exchange.


Make them the Co-Creator


Creating a steering committee of peer executives to advise on the program or connecting the program to a customer advisory board or council composed of those peers is another way to establish relevance with a targeted audience. You can also choose one or a few CxOs to be your advisor(s). Obtaining early input and guidance on what makes a compelling event agenda is effective to turn would-be attendees into co-creators and peer evangelists, and confirmed attendees.


I’ve found that running a quick survey can also be effective in engaging the C-Suite and increasing event attendance. By asking for their input on topics, agendas, event dates, and venue options, we can make them feel like they’re part of the planning process and it will increase their likelihood of attending.


Co-creation is the most effective tool for creating a compelling executive event. Participants who contribute to the program tend to promote and advocate the event, immediately enhancing its appeal.


Secure Anchor Attendees and Utilize them in your Follow Up


To drive C-Suite attendance, leverage the confirmation of your anchor C-Suite attendees by name-dropping them in your follow-up communications. Be sure to keep your sales team updated on the list of confirmed key attendees. Senior leaders appreciate knowing that they will be in the company of other high-profile attendees, which can create a sense of FOMO (fear of missing out) and increase the chances of their attendance.


Leverage Connections to Partners


You can leverage partner connections to drive attendance from senior executives. Partners can mean media groups, analysts, consulting partners, or non-competing solution providers. To reach a broader audience they can co-host the event if your offering aligns, or simply get them to recommend your event. Many media and analyst groups offer paid engagements.


Give them the Spotlight


Consider inviting executives to speak at your events to give them a chance to be in the spotlight.TIP: Even if you do not have an existing relationship yet with potential speakers, many executives welcome being presented as a thought leader. This is also a great way to establish a new relationship.


Consider Venue, Timing, and Format


When planning a C-Suite event, it’s crucial to consider several logistical factors, including the venue, timing, and format that will best suit your audience. While there may be some geographical variations, most C-Level events tend to last around two hours and are typically held at a centrally located (read: easily accessible) five-star hotel or other unique venues that align with the event’s theme or purpose. Depending on your audience’s preferences and the purpose of the event, you may want to consider hosting a breakfast event, a sit-down dinner, or an after-work networking cocktail. By selecting the right format, you can create an atmosphere that is conducive to productive discussions, networking, and knowledge-sharing. The venue should also be carefully chosen to align with the event’s objectives and provide a memorable experience for the attendees.


Get Creative with the Invitation


It’s all in the details. To make your C-Suite invitees feel truly special, consider designing a personalized invitation that includes unique elements of surprise. By investing in a beautifully crafted invitation that highlights the exclusivity of your event, you can create a sense of anticipation and excitement. Ensure that the invitation reflects the high-end experience that you aim to deliver, and make it clear that this is not just another event, but one that is tailored specifically for high-value individuals. If you have done a similar event in the past, do not hesitate to add social proof, for example, a quote from a previous CxO attendee who shares how valuable the event was for him or her.


Note: Creativity should be applied to all aspects of the event, too!


Focus on Engagement


When planning a C-Suite event, it’s critical to prioritize engagement over mere attendance. To ensure that your event is engaging and valuable to attendees, consider hiring a senior moderator with experience and comfort in engaging with C-Suite executives. A skilled moderator knows how to ask the right probing questions, stimulate discussion, and maintain the audience’s attention. By engaging your audience in meaningful and thought-provoking discussions, you can create a memorable experience that delivers real value to your attendees. Additionally, don’t forget to provide ample opportunities for networking and one-on-one discussions to facilitate relationship building. Remember, engagement is key to ensuring that your C-Suite customers come back for more and continue to view your brand as a trusted partner.


Don’t forget to include Social Events in your Mix


Additionally, social-focused invitations can also be effective in engaging C-level executives. Personal invitations to high-level activities such as charity or sports events, executive networking opportunities, or unique venues with their spouse or children- like a movie premier – can help create an appealing experience.


There you have it – strategies to engage the C-Suite! Did I miss anything? Feel free to write in the comments or DM me!


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