What counts as a CEO-led sales strategy in event tech?
When we talk about CEO-led sales in event tech, we are not talking about a founder swooping in to save deals at quarter end. A true CEO-led strategy is one where the CEO shapes the go-to-market motion by staying close to customers, influencing pricing and packaging, and modeling how the company listens and responds. It applies across in-person, virtual, and hybrid event businesses, from user conferences to internal meetings. To decide whether a sales motion is genuinely CEO-led, you can look at a few dimensions: how often the CEO speaks directly with customers, how clearly the ideal customer profile is defined, how much of pipeline comes from inbound signals, how creative and relevant outbound activities feel to buyers, and how well product decisions trace back to real conversations instead of internal guesswork. Jonathan’s conversation on “Sales Talk for CEOs” is a field guide for all of that.
Credit and source: This interview was originally published on the “Sales Talk for CEOs” podcast with Alice Heiman. Full original episode link :https://youtu.be/1w-7VdopCBU
This article pulls out the practical lessons from that interview so you can apply them to your own revenue strategy, then sends you back to the video if you want the full story.
The core signals of healthy CEO-led sales
Listening to Jonathan, five signals show up again and again. You can use them as a quick self-audit.
1. Support is part of the sales motion, not an afterthought
Very early on, his team added live chat to their site and committed to answering quickly, even before they had a formal outbound engine. That one decision changed who they heard from and how often. Prospects who might have bounced instead started conversations, and those conversations became customers.
For your own team, the question is simple: if someone from your dream account lands on your site at 10 p.m. with a question, does anything actually happen, or do they just get a form?
2. Pricing is tied to value, not insecurity
Jonathan is candid about undercharging in early years. They priced low because they felt their product could not justify the same levels as legacy vendors, even though for some customers they were already a better fit. It slowed growth and made reinvestment harder.
A CEO-led approach treats pricing as a strategic lever. You test it, you listen to customer reactions, and you adjust with evidence, not fear.
3. Customer conversations are regular, not rare
In the interview, Jonathan talks about long runs of back-to-back customer calls. Not as a one-off listening tour, but as part of his normal week. His favorite question is “Where are you spending most of your time?” because the answer exposes bottlenecks that dashboards never show.
If you are a CEO, you do not have to run every discovery call, but you should have a steady diet of unscripted customer conversations.
4. Outbound feels like an experience, not an interruption
Instead of relying on cold outbound sequences that ask busy executives for “30 minutes to see a demo,” his team leaned into something more aligned with their buyers: intimate dinners and executive gatherings where heads of events and field marketing can finally talk with peers. No pitch at the table, just real stories and shared problems.
5. Growth is bootstrapped by design, even if you have funding
The company was bootstrapped for years. That pressure forced discipline. They could not afford to build features for “cool factor” alone, or to ignore customers for quarters at a time. Whether you are bootstrapped or funded, adopting that mindset keeps your go-to-market grounded.
If you want to see how this thinking shows up in planning and marketing, this guide to field marketing strategy is a useful companion.
How Jonathan actually sells: real workflows and edge cases
A lot of CEO sales content stays at the level of slogans. The interview is more concrete.
Live chat as a discovery engine
Workflow in practice:
- A prospect lands on the website from search or word of mouth.
- Instead of being pushed immediately into a long form, they see a chat widget.
- They ask a specific question about a feature, use case, or implementation.
- A human answers in near real time and, when appropriate, offers to jump on a call.
Edge cases that matter:
- The person in chat might be a senior executive doing research late at night.
- They might be mid-contract with another vendor and only starting to explore.
- They might never fill out a form, but they will remember whether anyone helped them.
If your support and sales tools are disconnected, you miss these moments. A CEO-led motion treats every inbound contact as both a service opportunity and a window into how people discover you.
Executive dinners instead of cold outbound
Jonathan’s team runs a repeatable pattern in cities where they want to build pipeline.
Typical workflow:
- They identify 300 to 400 people in their ICP in a given city.
- They invite a subset to a 20 to 40 person dinner with a clear, peer-focused theme.
- Existing customers are invited alongside net-new executives.
- There is no stage presentation. The value is in the room.
Edge cases that block results if you ignore them:
- Many invitees are locked into multi-year contracts with other vendors. You will not “convert” them in 30 days, so attribution windows must be long.
- Some people say no to the dinner but still request a follow-up call, which means your tracking needs to catch more than attendance.
- Strong advocates can dominate the conversation if you are not careful, which is why having a mix of voices at each table matters.
This kind of outbound is slower and more intentional than high-volume sequences, but it matches the complexity and risk of changing event platforms. For more on this style of motion, the article on word of mouth marketing is worth a read.
Implementation details CEOs should not ignore
Even if you are not the one configuring events, a CEO-led sales strategy benefits from understanding a few implementation realities. These show up repeatedly in the questions Jonathan asks vendors and in how his own team works with customers.
Data and integrations
When a prospect asks for a demo, it is tempting to focus on the visual experience. Jonathan keeps returning to data. Where does it go. How does it get there. How easy is it for sales and marketing to use.
Implementation questions to keep on your short list:
- Which systems need to share data: CRM, marketing automation, finance, learning systems.
- How registrations, attendance, engagement, and leads will flow without manual exports.
- How quickly data updates propagate when something changes mid-event.
This is where having an event software RFP template can keep your team honest.
Onboarding and change management
Jonathan’s story also highlights that early customers were patient largely because they felt heard. As your company grows, you cannot rely on goodwill alone.
Things CEOs often underestimate:
- How many internal teams touch events: marketing, sales, IT, finance, education.
- How many of them need training when you change platforms.
- How much time event owners spend on manual workarounds that you never see.
During demos and pilots, ask your team afterward: “What would break if we tried to run next year’s flagship conference on this tomorrow?” The uncomfortable answers are where you need better onboarding plans.
Reporting and measurement
In the interview, Jonathan talks about moving from small events to larger, multi-year enterprise contracts. That shift only works if you can tell a clear performance story.
From a CEO perspective, “good” measurement usually includes:
- Event-sourced opportunities, not just badge scans.
- Sponsor and exhibitor outcomes, not just booth traffic.
- Content performance, including which sessions drive follow-up interest.
Many platforms offer activity dashboards, but you will want to see how those metrics translate into revenue conversations and renewal discussions, not just pretty charts. Articles like how event marketing can optimize sales show one way to frame this.
Security and compliance
The interview does not dwell on security, but if your events collect personal data or handle continuing education, this deserves CEO attention. At minimum, your evaluation and sales conversations should cover:
- How authentication is handled, including SSO options.
- How permissions and content gating work for different attendee types.
- How data retention, export, and deletion policies align with your wider privacy posture.
You do not need to memorize acronyms, but you should be fluent enough to ask good questions.
Cost and resourcing
Jonathan mentions undercharging for years and then correcting. On the buyer side, many teams do the opposite: they underestimate total cost.
As CEO, look past license price into:
- Internal time to implement and run the platform for each major event.
- Design, production, and content costs for the experiences you plan to host.
- The opportunity cost of staying with a platform that slows your team down.
A CEO-led sales strategy is honest about these tradeoffs on both sides.
Demo / POC checklist grounded in real evaluation
When you move from learning to buying, it is easy for demos to turn into scripted shows. Jonathan’s approach, and the Vendor Demo Guidelines his team uses, push you to treat demos more like working sessions.
Here is a checklist you can hand to your team before the next round of calls:
Integration and data handling
- Ask the vendor to push a sample registration into your CRM during the call.
- Have them show where session attendance and engagement will appear for sales.
- Confirm how often data syncs and what happens if something fails.
Agenda and content workflows
- Request a live build of a multi-track agenda with at least one parent and child session.
- Ask them to change the order of fields on a session details page while you watch.
- Have them demonstrate how last minute changes would be published on web and mobile.
User experience across web and app
- Have them show how an attendee builds a personal agenda and favorites sessions.
- Ask them to join a live or simulated session, adjust playback settings, and move between devices.
- Confirm how profiles, bookmarks, and schedules stay in sync between web and mobile.
Configuration and branding
- Ask them to create a new page, change navigation, and apply a simple branding update.
- Have them add a sponsor banner or simple ad placement to a specific page.
Reporting and analytics
- Request a walkthrough of user activity reports and sponsor or exhibitor reports.
- Confirm which data is available via API if you want to build your own dashboards.
Authentication, gating, and compliance
- Ask them to show how SSO is configured for attendees and staff.
- Have them build a simple rule where only certain ticket types can access a premium session.
Treat this checklist as a script for your team. The goal is not to “catch vendors out” but to verify how well each product fits the real work your event team does.
Putting it together
Jonathan’s Sales Talk for CEOs interview is a reminder that CEO-led sales is less about heroics and more about habits. Regular conversations with customers, honest pricing decisions, creative outbound that respects people’s time, and a deep understanding of workflows all compound over years.
If you watch the interview and then review your own sales motion, look for the gaps between what you think is happening and what buyers actually experience. Fill those gaps with better questions, better demos, and better follow through, and you will be much closer to the kind of growth story he describes.
FAQs
How can a CEO stay close to customers without derailing their own schedule?
The simplest way is to block recurring time for short customer conversations and treat them as non-negotiable. Rather than joining only high-stakes deals, schedule a mix of quick discovery calls and informal check-ins, then share what you learn with product and sales leaders. Over time, this creates a feedback loop that shapes roadmap and messaging without turning you into the bottleneck.
What is a realistic alternative to high volume cold outbound for event tech teams?
A realistic alternative is to design outbound around small, high value experiences such as executive dinners or peer roundtables. These gatherings give heads of events and field marketers a chance to connect with peers and share challenges, which builds trust much faster than generic email sequences. You can then follow up one to one with people who show interest instead of chasing unqualified leads.
How should event leaders evaluate platforms when data and integrations matter most?
Event leaders should enter demos with specific, concrete data scenarios rather than broad questions. Ask vendors to send a sample registration into your CRM, show where engagement metrics appear for sales, and demonstrate how changes propagate between systems. The more you anchor evaluation in your current tech stack, the easier it is to see whether a platform will reduce manual work or create more of it.
What can go wrong if CEOs stay away from sales and customer conversations for too long?
If CEOs stay away for too long, the company’s stories about customers drift away from reality. Product teams may build for imagined use cases, sales teams may repeat messages that no longer resonate, and pricing can lag behind the value the market is willing to pay. Periodic direct contact with customers keeps assumptions honest and surfaces patterns that never make it into formal reports.
How do I make sure vendor demos reflect our real event workflows, not a scripted show?
You can send vendors a short, focused brief that describes one or two real events and asks them to use those as the basis for their demonstration. During the call, ask them to make small configuration changes live, walk through integrations, and show reports that match your success metrics. This approach keeps the conversation grounded in your world and makes it much easier to compare vendors afterwards.
