Executive Roundtables: Our Highest-Converting Event Format

We ran a webinar on "Sales Enablement Best Practices." 480 attendees. Good engagement. 12-minute average viewing time.

We generated 38 qualified leads. Of those, 3 turned into opportunities.

Conversion rate: 0.6%

The next month, we tried something different. Instead of a 480-person webinar, we hosted an executive roundtable dinner.

12 attendees. All VP Sales or CROs. All at companies in our ICP. All personally invited by our sales team.

We generated 8 qualified opportunities from that dinner.

Conversion rate: 67%

Same topic (sales enablement challenges). Same company presenting (us). Completely different format and results.

The insight: Large events optimize for reach. Small roundtables optimize for conversion.

Executive roundtables became our highest-converting event format. Here's how we run them and why they work.

The Invite Strategy That Ensures Quality

The biggest difference between webinars and roundtables: Attendee selection.

Webinars: Open registration. Anyone can sign up. We hope qualified people attend.

Roundtables: Curated invite list. We personally select every attendee.

Our roundtable invite strategy:

Step 1: Define the ideal attendee profile

For each roundtable, we define exactly who should attend:

Example roundtable: "VP Sales Peer Discussion on Sales Enablement"

Ideal attendee:

• Title: VP Sales, CRO, or Sales Director
• Company size: 100-500 employees
• Industry: B2B SaaS
• Challenge: Scaling sales team, improving ramp time, or enablement gaps
• Status: Active opportunity OR target account we're pursuing

We aim for 12-15 attendees. We invite 25-30 to account for declines.

Step 2: Source attendees from multiple channels

Channel 1: Sales pipeline (50% of invites)

Sales gives us contacts from active opportunities:

• Deals in Stage 2-3 (qualified but not yet closed)
• Decision-makers or key influencers
• Accounts where we need to build momentum

Why this works: Roundtable accelerates existing deals by building relationships and addressing concerns in peer discussion.

Channel 2: Target accounts (30% of invites)

Sales gives us target accounts they're pursuing but haven't engaged deeply:

• Named accounts in territory plans
• Companies matching our ICP
• Accounts where we've struggled to get meetings

Why this works: Roundtable is a valuable, low-pressure entry point. Easier to say yes to "peer discussion" than "sales demo."

Channel 3: Customers (20% of invites)

We invite 2-3 customers to each roundtable:

• Successful implementations (social proof for prospects)
• Willing to share experiences (not just listen)
• Represent similar use cases to prospects attending

Why this works: Prospects trust peer experiences more than vendor claims. Customer participation validates our value.

Step 3: Personal outreach (not mass email)

Bad invite: "You're invited to our executive roundtable on sales enablement. Click here to register."

Generic. Feels like marketing spam.

Good invite:

"Hi [Name],

I'm hosting a small roundtable dinner next month for VP Sales leaders dealing with sales enablement challenges at scale.

Based on our conversations about [specific challenge you mentioned], I thought you'd find value in this discussion. We'll have 10-12 sales leaders from companies like [Similar Company A] and [Similar Company B] sharing how they're addressing:

• Sales ramp time reduction
• Enablement content that actually gets used
• Measuring enablement impact

Would you be interested in joining? It's intentionally small and peer-focused—no product pitches, just shared learning.

[Sales Rep Name]"

Why this works:

• Personal (references previous conversation)
• Specific (clear topics and value)
• Peer-focused (not a vendor pitch)
• Curated (mentions other attendees' companies)

Response rate: 42% acceptance rate (vs. 8% for webinar invites)

The result: 12 highly qualified attendees, all in our ICP, all with active challenges we solve.

The Discussion Facilitation That Drives Value

The second difference: Format. Roundtables aren't presentations—they're facilitated peer discussions.

What doesn't work:

Mistake 1: Vendor presentation disguised as roundtable

We present for 40 minutes, then ask "Any questions?" Nobody asks questions because it felt like a pitch.

Mistake 2: Unstructured "open discussion"

We say "Let's discuss sales enablement challenges" with no structure. Conversation meanders. Dominant personalities take over. Quiet attendees don't participate.

What works: Structured facilitation with open discussion

Our roundtable facilitation framework:

Minutes 0-15: Introductions and context setting

Facilitator (our CEO or sales leader):

"Welcome everyone. We've brought together 12 sales leaders all facing similar challenges around scaling sales teams and enablement. Here's how today will work:

• This is a peer discussion, not a presentation
• We're here to learn from each other
• Everyone's experiences are valuable—please share openly
• What's said here stays here (Chatham House Rule)
• We'll cover [3 key topics] in 90 minutes

Let's start with quick intros: Name, company, and the #1 sales enablement challenge you're facing right now."

Why this works:

• Sets expectations (peer discussion, not pitch)
• Creates psychological safety (Chatham House Rule)
• Agenda provides structure
• Intros reveal common challenges

Minutes 15-35: Topic 1 Discussion

Facilitator introduces the topic:

"The #1 theme from your intros: Sales ramp time is too long. Who wants to share how long it takes your reps to ramp, and what's causing the delay?"

Discussion flow:

• 2-3 people share their situations
• Facilitator asks follow-up questions
• Other attendees chime in with similar experiences or solutions
• Customer attendees share what worked for them

Facilitator role:

• Draw out quiet attendees: "Sarah, have you dealt with this?"
• Keep discussion on topic
• Capture key insights on whiteboard
• Synthesize common themes

Why this works:

• Peer learning (not vendor telling)
• Real challenges and solutions shared
• Everyone contributes

Minutes 35-55: Topic 2 Discussion

Same format, different topic.

Example topic: "Enablement content creation: How do you keep it updated and ensure reps actually use it?"

Minutes 55-75: Topic 3 Discussion

Same format, different topic.

Example topic: "Measuring enablement impact: How do you prove ROI to your CFO?"

Minutes 75-85: Synthesis and key takeaways

Facilitator summarizes:

"Here's what I heard as common themes:

1. [Theme 1]
2. [Theme 2]
3. [Theme 3]

And here are tactical approaches that several of you mentioned:

• [Tactic 1]
• [Tactic 2]
• [Tactic 3]

Anything I missed?"

Why this works:

• Attendees leave with clear takeaways
• Reinforces value of peer discussion
• Creates shared understanding

Minutes 85-90: Next steps and follow-up

Facilitator:

"This was incredibly valuable. A few next steps:

1. I'll send a summary of today's discussion to everyone
2. If anyone wants to continue these conversations, I'm happy to connect you
3. For those interested in seeing how [our product] addresses some of these challenges, I'm happy to schedule a follow-up call

Thank you for sharing so openly."

Why this works:

• Soft CTA (not pushy)
• Offers value (discussion summary, peer connections)
• Opens door for sales follow-up

The result: Attendees feel they learned from peers, not that they sat through a sales pitch.

The Peer Learning Strategy That Builds Trust

The third key: Roundtables create peer learning, not vendor education.

Why peer learning converts better:

Trust differential:

• Vendor claim: "Our product reduces ramp time by 40%" → Skepticism
• Peer experience: "We implemented [product] and our ramp time went from 90 days to 54 days" → Credible

Relevance:

• Vendor generic: "Here's how sales enablement works" → Mildly interesting
• Peer specific: "Here's exactly how we solved the ramp time problem with our remote team" → Actionable

Emotional connection:

• Vendor transactional: Sales rep pitching
• Peer relational: Executives helping each other solve real problems

Our peer learning tactics:

Tactic 1: Invite customers to every roundtable

We invite 2-3 customers who:

• Have achieved results with our product
• Are willing to share their journey (including challenges)
• Represent similar use cases to prospects attending

Their role:

• Share their experience honestly (not a testimonial script)
• Answer questions from prospects
• Provide peer validation

Example:

Prospect asks: "How long did implementation take?"

Customer responds: "For us, it was 6 weeks. The first 2 weeks were rough—lots of change management. But our CSM helped us through it, and by week 4 we were seeing adoption."

This is more credible than any vendor claim.

Tactic 2: Facilitate peer-to-peer connections

After the roundtable:

• We connect attendees who expressed similar challenges
• We facilitate follow-up conversations
• We create a Slack channel for ongoing peer discussion

Why this works: The value extends beyond the event. Attendees build relationships with peers facing similar challenges.

Tactic 3: Focus discussion on challenges, not solutions

We don't lead with "here's how to solve this." We lead with "what are you struggling with?"

This approach:

• Makes prospects feel heard
• Surfaces their real pain points
• Allows customer attendees to share solutions organically
• Positions our product as the natural answer to challenges being discussed

The result: By the end of the roundtable, prospects have heard from peers that the challenges they're facing are solvable, and they've seen evidence that our product helps.

We don't have to pitch. Peer learning does the selling.

The Follow-Up Conversion Strategy

The fourth key: What happens after the roundtable.

Our follow-up sequence:

Day 1 (Same day as roundtable):

Email from facilitator to all attendees:

"Subject: Thank you + Discussion Summary"

"Thank you for joining today's roundtable. The discussion was incredibly valuable.

Here's a summary of key themes and takeaways: [bullet points]

A few people mentioned interest in continuing the conversation. I'm happy to connect you:

• [Person A] and [Person B] both mentioned [topic]—I'll introduce you
• [Person C] offered to share their [framework]—I'll send that separately

For those interested in exploring how [our product] addresses some of the challenges we discussed, I'm happy to schedule a follow-up call. Just reply to this email.

Thanks again for your openness and insights.

[Facilitator Name]"

Why this works:

• Provides immediate value (summary)
• Facilitates peer connections (extends relationships)
• Soft CTA for product conversation (low pressure)

Day 3 (For prospects who attended):

Personal email from their account exec:

"Subject: Following up on the roundtable"

"Hi [Name],

I heard you attended our sales enablement roundtable earlier this week. [Facilitator] mentioned you shared some interesting challenges around [specific topic].

Based on what you mentioned, I thought you might find value in seeing how [Customer who attended] is addressing that exact challenge with [our product]. Would you be open to a 20-minute call where I walk through their implementation?

I'm looking at Tuesday at 2 PM or Thursday at 10 AM. Which works better?

[Sales Rep]"

Why this works:

• Personalized (references their specific challenge)
• Peer validation (mentions customer who attended)
• Specific next step (20-minute call with specific times)

Conversion rate: 67% of roundtable attendees book follow-up calls (vs. 8% of webinar attendees)

Day 7 (For attendees who booked follow-up):

Demo call focused specifically on the challenges they raised in the roundtable.

Day 14 (For attendees who didn't book follow-up):

Email offering additional value:

"Hi [Name],

Quick follow-up—several attendees from the roundtable asked for more detail on [topic we discussed]. I put together a guide that goes deeper: [link]

If you'd like to discuss how this applies to [their company], I'm happy to chat. Otherwise, hope the guide is helpful.

[Sales Rep]"

The follow-up conversion funnel:

• 12 roundtable attendees
• 8 book follow-up calls (67%)
• 6 become qualified opportunities (50% of attendees)
• 3 close within 90 days (25% of attendees)

Compare to webinar funnel:

• 480 webinar attendees
• 38 book follow-up calls (8%)
• 12 become qualified opportunities (2.5% of attendees)
• 3 close within 90 days (0.6% of attendees)

Roundtables convert at 42x the rate of webinars.

The Scaling Strategy That Maintains Intimacy

The challenge: Roundtables convert incredibly well, but they don't scale like webinars.

How do you maintain the intimacy and conversion power while increasing volume?

Our scaling approach:

Run multiple small roundtables, not one large event

Instead of:

• 1 webinar with 500 attendees

We run:

• 10 roundtables with 12 attendees each (120 total attendees)

The math:

• Webinar: 500 attendees, 0.6% conversion = 3 opportunities
• Roundtables: 120 attendees, 50% conversion = 60 opportunities

Roundtables generate 20x more opportunities despite 76% fewer attendees.

Regional execution

We empower regional sales teams to run their own roundtables:

• Provide facilitation guide and discussion topics
• Supply customer speakers from their region
• Give budget ($1,500-2,500 per roundtable)

Result: We went from 2 roundtables per quarter (HQ-run) to 18 roundtables per quarter (regionally distributed).

Vertical-specific roundtables

Instead of generic "sales enablement" roundtables, we run:

• Healthcare sales leaders roundtable
• FinTech sales leaders roundtable
• E-commerce sales leaders roundtable

Why this works:

• More specific peer learning (healthcare challenges are different from fintech)
• Easier to curate attendees (clear selection criteria)
• Higher perceived value (vertical-specific insights)

Virtual roundtables for broader reach

For prospects who can't attend in-person:

• Virtual roundtables (12 attendees on Zoom)
• Same facilitation format
• Lower cost ($500 vs. $2,000 for in-person dinner)

Conversion rate: 45% (slightly lower than in-person 67%, but still excellent)

What Actually Works for Executive Roundtables

After running 50+ roundtables, here's what drives conversion:

Curate attendees ruthlessly. 12 qualified attendees beat 500 random registrants. Personal invites from sales reps, not mass email.

Facilitate, don't present. Structured peer discussion, not vendor presentation. Customers share experiences, not just vendor claims.

Include customers in every roundtable. 2-3 customers provide peer validation and social proof.

Focus on challenges, not solutions. Lead with "what are you struggling with?" Solutions emerge organically from discussion.

Follow up personally within 24 hours. Discussion summary, peer connections, soft CTA for product conversation.

Scale through regional execution. Empower sales teams to run their own roundtables with playbooks and support.

Run vertical-specific roundtables. Healthcare, FinTech, E-commerce—specific beats generic.

Track conversion, not attendance. 12 attendees → 8 opportunities is better than 500 attendees → 3 opportunities.

Before roundtables:

• Event strategy: Monthly webinars, 400-500 attendees each
• Conversion rate: 0.6-1.2%
• Opportunities per event: 3-5
• Cost per opportunity: $2,400

After roundtables:

• Event strategy: 18 roundtables per quarter, 12 attendees each
• Conversion rate: 50-67%
• Opportunities per event: 6-8
• Cost per opportunity: $320

Roundtables became our highest-ROI event format.

The uncomfortable truth: Most companies optimize for reach (how many people can we get in a room) instead of conversion (how many become customers).

Large events feel impressive. "We had 500 attendees!" sounds good in an exec meeting.

But 12 curated attendees who convert at 67% generate more revenue than 500 random attendees who convert at 0.6%.

Stop optimizing for attendance. Start optimizing for conversion.

Run smaller, curated roundtables where real peer learning happens.

Your sales team will thank you.