Event strategy and measurement

Event Strategy and Measurement

Overview

This skill covers B2B event strategy and measurement, including conference participation, hosted events, webinars, and event ROI frameworks. All practices are sourced exclusively from Exit Five podcast guests across 39 episodes. Where guests disagree on fundamental questions — booth vs. no-booth, gated vs. ungated webinars, immediate vs. long-term ROI measurement — those disagreements are preserved and presented in full rather than resolved.

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Strategic Planning: Before You Execute

Start with strategy, not execution. The biggest mistake is moving too quickly and packing the event program too full without thinking end-to-end. Before executing, take time to be strategic about what you're trying to accomplish, who you want in the room, and how you'll measure success. (Source: Stephanie Christensen, Episode #227)

Define the event's purpose before setting metrics. Not all events serve the same purpose. Brand events should be measured by awareness, pitch testing, and prospect engagement rather than immediate lead generation. Demand events should focus on meeting bookings and pipeline. Clarify the event's purpose upfront to set appropriate success metrics and avoid misaligning expectations with sales teams expecting immediate ROI from brand-focused activations. (Source: Holly Xiao, Episode #270)

Explicitly weight multiple event goals. When an event has multiple objectives (pipeline, brand, customer retention), assign percentage weights to each goal and communicate these weights to your team before execution. For example, if pipeline is your primary goal, weight it at 75%, brand at 15%, and customer retention at 10%. This prevents misalignment during planning and helps you make trade-off decisions about where to invest effort and resources. (Source: Kera Wright, Episode #124)

Validate before investing in experiential activations. Don't start with events if you're still proving out a channel. First, validate with quantifiable, measurable campaigns (sponsored posts, webinars) that show clear ROI. Once you have proof of concept and budget approval, then invest in longer-term relationships and experiential activations. (Source: Brianna Doe, Episode #305)

Before booking a venue, document the event's brand positioning statement and location rationale as you would a product brief, and revisit it year-over-year to build consistent brand identity. Apply product thinking to events: invest in the venue, brand, and experience as a long-term asset rather than a transactional project. Make strategic decisions about location and positioning that become part of the brand identity. (Source: Dave Gerhardt, Episode #294)

Build your event calendar by analyzing where your customers already come from. Start by analyzing which existing platforms, technologies, or events your best customers are already using or attending. If your customers heavily use Salesforce and HubSpot, prioritize sponsoring or hosting events at Dreamforce and INBOUND rather than creating entirely new events from scratch. (Source: Kera Wright, Episode #124)

Structure annual marketing narrative around 2-3 messaging pillars, rotating focus across events. Define 2-3 core messaging pillars that support your overall positioning. Assign each pillar to specific events or time periods throughout the year. Ensure every event, campaign, and piece of content ladders back to whichever pillar is in focus. (Source: Kira Federer, Episode #254)

Evaluate webinar viability by working backward from customer motivation. Rather than dismissing webinars as outdated, ask: "Why would someone take an hour out of their day to attend this webinar?" Webinars remain viable if they satisfy one of five core motivations: make me look good, save time, make money, avoid pain, reach next level. If you cannot articulate which of these motivations your webinar satisfies in one sentence, don't run it. (Source: Dave Gerhardt, Episode #311)

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Event Format Selection

Hosted Intimate Events

Host VIP dinners for enterprise pipeline generation. Host intimate, curated dinners (approximately 16 people including your team) in major cities where your ICP is concentrated. Invite a mix of existing customers (2-3) and prospects via warm intros and cold outreach. Structure the dinner with intentional seating, have the CEO frame market challenges and explain the product briefly, then facilitate peer introductions where attendees share their role and one big bet around your product category. Follow up with photos from the dinner and social amplification to create FOMO for future events. (Source: Natalie Taylor, Episode #162)

Design dinner events with embedded discovery conversations. Structure events around a specific, interesting topic broad enough to attract your ICP but structured so that discovery conversations happen during the event itself. By the end of the event, aim for at least 50% of attendees to express interest in a demo or further conversation. (Source: Natalie Taylor, Episode #306)

Host intimate dinners combining customers and prospects. Organize small, in-person dinners combining a small number of existing customers (2) with a larger group of prospects (approximately 10). The in-person connection and 2-3 hour engagement creates meaningful relationship-building. (Source: Dave Gerhardt, Episode #214)

Host ancillary events around major industry conferences. Instead of building a large event from scratch, identify major industry conferences where your target audience will already be attending. Host smaller, more intimate ancillary events (dinners, happy hours, breakfasts) nearby during the conference. This leverages existing attendee traffic, reduces marketing spend on getting butts in seats, and allows you to create a more curated, high-touch experience. (Source: Stephanie Christensen, Episode #227)

Layer intimate experiences into large-scale event strategies. Beyond large-scale events, layer in intimate experiences: executive dinners the night before, lunches with specific customer segments, curated group experiences. These face-to-face touchpoints drive disproportionate conversion despite lower volume. Use events as part of a multi-touch journey, not as direct-response channels. (Source: Kelly Hopping, Episode #255)

(Note: whether intimate hosted events or trade show booths are better for pipeline generation is contested — see Where Experts Disagree)

Conference Participation and Booth Strategy

Use breakfast and off-site lunch sponsorships as alternatives to booth investments. Rather than investing $50,000+ in a conference booth, sponsor breakfast or off-site lunch events to create intimate settings with prospects and customers. Breakfast reaches attendees before their day gets derailed; off-site lunches avoid the crowded, rushed conference hall experience. These activations are typically less costly than booth sponsorships while enabling meaningful one-on-one conversations. (Source: Sandra Rand, Episode #265)

Build brand recall through repeated logo exposure across multiple event sponsorships. Instead of investing heavily in one major event activation, distribute budget across multiple smaller sponsorships (lanyard sponsorships, breakfast sponsors, etc.) at the same events year-over-year. This creates repeated logo exposure that compounds brand recognition and recall over time. (Source: Sandra Rand, Episode #265)

Run pre-conference branded ads to conference attendees without a booth. When attending a conference without a booth, use pre-event sponsorship (e.g., happy hour) to access the attendee list. Upload the list to LinkedIn ads and Vector. Run two ad variants: one generic conference message and one featuring your branded swag/product. Direct traffic to a simple landing page. Use Vector to identify which attendees visited your site. Send personalized follow-up emails to site visitors offering to meet at the conference. Tess's results: $1K ad spend, 65% of attendees visited site (vs. typical 35% booth traffic), 11 on-site meetings, 3 open deals, 2,000% ROI. (Source: Tess Pfeifle, Episode #341)

Host your own events at major conferences instead of buying booth space. Rather than spending $50K+ on a conference booth, host your own event (dinner, workout session, interview recording) at the conference venue. This creates deeper relationships with target customers and generates content at a fraction of the cost. (Source: Dave Gerhardt, Episode #189)

(Note: whether to invest in a conference booth or replace it with alternative activations is contested — see Where Experts Disagree)

For physical B2B products, use a mix of trade shows, partner-hosted events, and company-hosted roadshows. Physical product marketing should include multiple event formats: major trade shows (e.g., Infocom, ISE); alliance partner events (e.g., Zoomtopia, Microsoft Ignite); and company-hosted roadshows that can be co-branded with partners to drive attendance. Implement rigorous payback analysis and metrics for each event to justify the expense. (Source: Priscilla Barolo, Episodes #302 and #193)

For events, choose a small number of marquee conferences where you can make a significant impact, and skip others entirely. Instead of attending many events with minimal presence, identify 1-2 major conferences per year where your target buyers will be present and commit significant budget, time, and creative resources. Explicitly choose not to attend other events where you cannot compete effectively. (Source: Mychelle Mollot, Episode #182)

(Note: how large events should be and how to allocate resources across them is contested — see Where Experts Disagree)

Creative and Non-Traditional Event Formats

Run events with creative, non-pitch formats. Move beyond traditional pitch-heavy events by designing unique formats that give attendees a reason to show up beyond product education. Examples include: musician performances paired with casual networking (no pitch), webinars where presenters paint while discussing topics (Bob Ross style), or intimate dinners with like-minded professionals. Pair these with strong SDR follow-up post-event to convert relationships into pipeline. (Source: Jason Lyman, Episode #263)

Reframe webinars as one-of-a-kind brand launch events. Move away from standard webinar formats and instead create unique, memorable live events designed as brand launches. Examples include: award shows (Dundies-style), product launches, GTM demo days, or other novel formats. Measure success by: (1) attendance lift, (2) brand search volume spikes, (3) sales team feedback on deal acceleration, and (4) ability to reactivate cold prospects by using the event as a conversation starter. (Source: Madhav Bhandari, Episode #183)

Use micro-influencer humor videos as paid ads to drive event attendance. Partner with micro-LinkedIn creators (10,000-15,000 followers) to create funny, 1-minute video skits promoting your event. Run these videos both organically and as paid ads. Humor is effective for reaching a wide audience with low cost-per-click. Example: ~$0.50 cost-per-click achieved with this approach. (Source: Madhav Bhandari, Episode #183)

Run smaller, activity-based in-person events (poker nights, hikes, pickleball) rather than large conferences to facilitate genuine peer connection. These formats create opportunities for authentic conversation that information-exchange formats don't. (Source: Kieran Flanagan, Episodes #318 and #257)

Host proprietary events to establish market presence when your category is not yet defined. When your product category doesn't have established analyst recognition (e.g., no Gartner Magic Quadrant), create your own events to build visibility and establish thought leadership. (Source: Mychelle Mollot, Episode #182)

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Event Scale and Portfolio Management

Build a diversified event portfolio across in-person, trade shows, virtual, and webinars. Rather than relying on one type of event, create a balanced portfolio that includes in-person events, trade show sponsorships, virtual events, and webinars. This diversification spreads risk, reaches different audience segments, and provides multiple touchpoints throughout the year. (Source: Stephanie Christensen, Episode #227)

Manage all events (first-party, third-party, partner) as an integrated system under one team. Consolidate all event management—regardless of size, format, or source—under a single team. This includes corporate events, partner events, and sponsored events. Treat events as a system designed to accomplish specific outcomes rather than as isolated tactical executions. This centralization enables consistent strategy, better resource allocation, and clearer measurement. (Source: Gurdeep Dhillon, Episodes #280 and #203)

Do not host a flagship customer conference unless you can fill it with at least 500 attendees. A half-empty event damages brand perception more than not hosting at all. If you don't have the customer base or prospect pool to fill a venue, run smaller roadshows or regional events instead until you've built sufficient scale. (Source: Stephanie Christensen, Episode #227)

(Note: the question of optimal event size involves contested positions — see Where Experts Disagree)

Keep events small (under 200-300 people) and focused; avoid scaling events as a primary revenue stream. Events under 200-300 people are manageable and can be profitable. Once you scale beyond that, the operational complexity and cost explode—you need union labor, expensive venues, catering, AV, and dozens of vendors. Cap events at 20% of total revenue and don't expect them to be profitable at scale. (Source: Jason Lemkin, Episodes #207 and #142)

(Note: this is contested — see Where Experts Disagree)

Position events as a community enabler and networking tool, not as a primary revenue source. Events should serve your community and enable networking, not be designed primarily to generate revenue. Revenue should come from other sources (sponsorships, memberships, media). (Source: Jason Lemkin, Episodes #207 and #142)

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Attendee Recruitment and Pre-Event Activation

Have marketing take direct responsibility for recruiting event attendees, not just sales. Use a multi-channel approach: send emails, post on LinkedIn, and text (if you have contact info) to personally invite prospects and customers. Quality of attendees matters more than quantity. (Source: Sydney Sloan, Episode #289)

Co-host events with complementary companies to share promotion burden and expand reach. Partner with a complementary company (one that serves the same audience but doesn't compete directly) to co-host. This splits the marketing lift, expands your reach to their audience, and often reduces costs by sharing venue or logistics. (Source: Kera Wright, Episode #124)

Leverage partners to amplify brand through events in geographies where you lack presence. When you have strong relationships with partners, they can organize events and webinars with you, allowing your brand to reach geographies where you don't have direct presence. (Source: Domi de Saint-Exupéry, Episode #332)

Embed webinar signup forms directly in related blog posts for organic registration lift. When you publish a blog post on a topic you'll later cover in a webinar, embed the webinar signup form or link at the top of that blog post. This leverages existing organic traffic to drive webinar registrations passively. Example: a blog post averaging 500-600 webinar registrants drove nearly 1,000 signups when the webinar form was embedded, with no additional email touchpoints required. (Source: Amanda Natividad, Episode #205)

Use content performance data to inform webinar and event topics. Analyze which content pieces are getting the most engagement on LinkedIn, driving the most website traffic, and converting best. Use these signals to identify topics for webinars and live events. (Source: Kyle Coleman, Episode #206)

Attend industry events to identify content topics and audience pain points. Walk the floor, observe which booths draw crowds, talk to attendees about their challenges, and take detailed notes on the topics and problems people care about most. Use these insights to generate 15-20 content ideas for the year ahead. (Source: Matt Carnevale, Episode #155)

Send cross-functional teams to industry conferences to absorb customer language. Bring demand gen, operations, product, and other non-traditional event attendees to conferences so they can directly observe how customers speak about their problems. This firsthand exposure translates into better messaging, positioning, and product decisions across the organization. (Source: Sandra Rand, Episode #265)

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Webinar Strategy

Choose webinar topics based on marketing goal: top-funnel awareness vs. mid-funnel product consideration. Define your goal first. If you want database growth and general awareness, use broad top-funnel topics (e.g., "What Everyone Needs to Know About X in 2026"). If you want to drive product sales, use mid-funnel topics that address specific problems your product solves. Mid-funnel webinars will have lower registration but higher-quality leads closer to purchase intent. (Source: Jay Schwedelson, Episode #329)

Use "attend to receive" incentives to boost webinar show rates by 30%+. Bake an exclusive incentive into webinar marketing that attendees only get if they show up live. Examples include: Q2 summary guides, beta access to new product releases, or live Q&A sessions. This must be front-and-center in marketing materials, not buried. Data shows this increases show rates by over 30% and drives 4x higher pipeline conversion compared to on-demand viewing. Attendees must stay for at least 50% of the session to trigger the incentive. (Source: Jay Schwedelson, Episode #329)

(Note: whether to gate webinars and optimize for live attendance vs. ungate to maximize reach is contested — see Where Experts Disagree)

Use a tangible incentive (free lunch, swag, tickets) to drive webinar registration and attendance. If webinar signups are low, offer a concrete incentive to the first N registrants. This can significantly boost both registration and attendance rates. (Source: Matt Carnevale, Episode #155)

Run ungated webinars focused on delivering value rather than lead capture, with personalized follow-up based on engagement signals. Remove gating from webinars to maximize attendance and audience reach. Focus the webinar itself on delivering genuine value and education rather than product pitches. Use personalized follow-up emails based on three data points: (1) how many webinars the person has attended, (2) what you know about them from website behavior and previous interactions, and (3) questions they asked during the webinar. Tailor each follow-up asset accordingly—recaps for no-shows, deeper product demos for advanced attendees, research-backed insights for top-of-funnel prospects. Measure success through engagement metrics (open rates, click-through rates) and longer-term pipeline influence with a 30-90 day lag to demo booked or closed deal, rather than optimizing for immediate demo bookings. (Source: Eoin Clancy, Episode #326)

(Note: this is contested — see Where Experts Disagree)

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Post-Event Follow-Up

Drop event leads into your CRM and send initial follow-up the same night of the event. Being the first to respond signals that your company is responsive and on top of things. Coordinate your post-event workflow so that lead capture, data entry, and initial outreach happen within hours of the event ending. (Source: Sydney Sloan, Episode #289)

Ensure strong SDR follow-up processes post-event to capture leads and prevent them from slipping through cracks. Document wins that trace back to past events to validate long-term ROI and build credibility for continued investment. (Source: Jason Lyman, Episode #263)

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Event ROI Measurement

Define primary growth metrics and secondary brand metrics for each event. For each event, identify your primary metric (usually revenue-related: pipeline, bookings, NRR) and secondary metrics (brand awareness, NPS, social mentions, press coverage). Stay focused on the primary metric while tracking secondary metrics. (Source: Stephanie Christensen, Episode #227)

Align event metrics to the funnel stage the event targets (TOFU, MOFU, BOFU). Top-of-funnel events (e.g., trade shows) should be measured on pipeline generation and new leads. Middle-of-funnel events (e.g., roadshows) should be measured on bookings and renewal rates. Bottom-of-funnel events (e.g., customer events) should be measured on product adoption, NPS, and expansion. (Source: Kristina DeBrito, Episode #227)

Measure event ROI across three pillars: revenue, target account penetration, and retention/expansion. Track: (1) new revenue and pipeline generated, (2) penetration of target accounts (getting the right people in the room), and (3) retention and expansion metrics (NRR, renewal rates, customer health). (Source: Stephanie Christensen, Episode #227)

Measure event ROI by calculating the total prospect revenue and retention revenue represented by attendees in the room. This metric justifies event investment by showing direct revenue exposure. Mix prospect and existing customer attendance intentionally—happy customers sell prospects on value. Track this metric across events to demonstrate cumulative impact (e.g., touching 20% of total company revenue across a multi-city roadshow). (Source: Sydney Sloan, Episode #289)

(Note: whether to measure event ROI immediately or over multiple quarters is contested — see Where Experts Disagree)

Use source attribution for top-of-funnel events and influenced attribution for middle/bottom-funnel events. For top-of-funnel events (e.g., trade shows), measure source attribution—the event is the first touch. For middle and bottom-of-funnel events (e.g., roadshows, customer events), measure influenced attribution—the event influenced the deal but wasn't necessarily the first touch. (Source: Kristina DeBrito, Episode #227)

Measure event quality using NPS, not just ticket sales. Send an NPS survey immediately after the event to quantify attendee satisfaction. Treat the event like any other product—measure it on NPS alongside other metrics like tickets sold. This gives you a benchmark to track improvement year-over-year. (Source: Dave Gerhardt, Episode #294)

Measure brand-focused events through site traffic, social mentions, press coverage, and NPS. For events where the primary goal is brand awareness (not direct revenue), measure secondary metrics like website traffic post-event, social media mentions, press coverage, app usage, and NPS score changes. (Source: Stephanie Christensen, Episode #227)

Measure customer event impact through product adoption, health scores, NPS, and renewal rates. For customer-focused events, measure success through customer-centric metrics: product adoption rates, health score improvements, NPS changes, renewal rates, and expansion revenue. (Source: Kristina DeBrito, Episode #227)

Track and communicate the correlation between event attendance and annual sales quota achievement. Measure and share data showing how many accounts need to attend your event for a sales rep to hit their annual quota. This ties event attendance directly to rep compensation and success. (Source: Stephanie Christensen, Episode #227)

Implement systematic tracking of which events attendees came from and correlate to pipeline and demos. Most companies don't track this data at all, making it impossible to measure event ROI. Once you have the data, use correlation analysis to quantify event impact. (Source: Pranav Piyush, Episode #191)

Measure event ROI over medium to long-term influence, not just immediate pipeline. Recognize that some marketing efforts (especially events) deliver pipeline over 2-3 quarters, not immediately. Establish a portfolio approach where you measure and track influence from events over time, working with sales and finance to set expectations that results will accrue over multiple quarters. (Source: Jason Lyman, Episode #263)

(Note: this is contested — see Where Experts Disagree)

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Getting Executive Buy-In for Events

Tailor event strategy presentations to match how executives process information. Different executives have different communication preferences. Some are visual thinkers (use mood boards and design mockups), others are analytical (use data and metrics). Understand how your executive stakeholders prefer to receive information and tailor your presentation accordingly. (Source: Stephanie Christensen, Episode #227)

Invite skeptical executives to attend events in the field to experience attendee value firsthand. If an executive is skeptical about your event strategy, don't just present data. Invite them to attend an event and interact with attendees directly. Seeing firsthand how much value attendees are getting is more persuasive than any presentation. (Source: Kristina DeBrito, Episode #227)

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Where Experts Disagree

1. Should you invest in a conference booth, or replace it with alternative activations?

Support summary: 4 (skip booth) vs. 2 (use booths)

Position A — Skip the booth; use alternative activations: Dave Gerhardt (Episode #189) argued that hosting your own event (dinner, workout session, interview recording) at the conference venue creates deeper relationships and generates content at a fraction of the cost of a $50K+ booth. Sandra Rand (Episode #265) recommended sponsoring breakfast or off-site lunch events instead, citing more intimate settings and meaningful one-on-one conversations at lower cost. Tess Pfeifle (Episode #341) achieved 2,000% ROI with $1K ad spend and no booth—65% of attendees visited her site vs. typical 35% booth traffic—by using pre-event branded ads and personalized follow-up to drive 11 on-site meetings. Andrew Davies (Episode #195) recommended replacing large trade shows with intimate dinners or multi-day retreats, citing higher-quality leads versus mixed-quality trade show leads requiring heavy post-event filtering.

Position B — Use booths and trade shows for new pipeline: Kera Wright (Episode #124) explicitly stated that trade shows (not hosted events) are the primary vehicle for generating new qualified pipeline from cold prospects, because attendees are already in a transactional mindset and expect to learn about products. Priscilla Barolo (Episodes #302 and #193) argued that in-person events and trade shows are critical for physical product marketing because customers need to touch the product and ask situation-specific questions that can't be answered via datasheets.

Context dependency: Priscilla Barolo's position is explicitly scoped to physical B2B products where tactile product experience is necessary. Kera Wright's position applies to cold pipeline generation specifically. The alternative-activation advocates are largely speaking about software/SaaS contexts. However, Dave Gerhardt, Sandra Rand, and Tess Pfeifle are making a general claim that booths are overpriced relative to alternatives, which conflicts with Kera Wright's general recommendation even in software contexts.

Trend note: The most recent guests (Tess Pfeifle, ep. 341, 2026; Sandra Rand, ep. 265, 2025) cluster on the skip-booth side, while the booth-positive voices (Kera Wright, ep. 124, 2024; Priscilla Barolo, ep. 302, 2025) are older or product-specific. This may reflect a growing preference for alternative activations over time.

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2. Should event ROI be measured immediately (pipeline sourced) or over a longer time horizon (influenced pipeline)?

Support summary: 4 (long-horizon) vs. 3 (immediate pipeline)

Position A — Measure event ROI over multiple quarters: Jason Lyman (Episode #263) argued that events deliver pipeline over 2-3 quarters, not immediately, and recommended documenting wins that trace back to past events to validate long-term ROI. Eoin Clancy (Episode #326) recommended measuring webinar/event success through longer-term pipeline influence with a 30-90 day lag to demo booked or closed deal. Ruth Zive (Episode #175) argued events deliver strong ROI when used for influence on existing pipeline rather than first-touch sourcing, implying measurement should focus on deal acceleration and influence rather than immediate pipeline sourced. Dave Gerhardt (Episode #294) argued that the real ROI of in-person events is the community and relationships built, which compound over time and drive word-of-mouth growth.

Position B — Measure event ROI on immediate pipeline and revenue in the room: Sydney Sloan (Episode #289) recommended measuring event ROI by calculating total prospect revenue and retention revenue represented by attendees, and tracking this metric across events to demonstrate cumulative impact. Kristina DeBrito (Episode #227) recommended aligning event metrics to funnel stage, with top-of-funnel events measured on pipeline generation and new leads, and middle-of-funnel events measured on bookings and renewal rates—all relatively near-term metrics. Stephanie Christensen (Episode #227) recommended measuring event ROI across three pillars including new revenue and pipeline generated as the primary metric.

Context dependency: The long-horizon camp may be more applicable to brand-building or top-of-funnel events, while the immediate-pipeline camp may be more applicable to field events and roadshows targeting warm prospects. However, both camps include guests speaking about similar event types (field events, roadshows), making this a genuine disagreement about measurement philosophy, not just context.

Trend note: No clear chronological trend identified.

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3. Are trade shows or hosted intimate events (dinners, retreats) better for pipeline generation?

Support summary: 4 (intimate events) vs. 2 (trade shows)

Position A — Intimate hosted events are better for pipeline: Andrew Davies (Episode #195) recommended replacing large trade shows with intimate dinners (10 founders) or multi-day retreats, citing higher-quality leads and customer relationships versus mixed-quality trade show leads requiring heavy post-event filtering. Natalie Taylor (Episode #162) described a VIP dinner strategy (16 people, mix of customers and prospects) as a primary enterprise pipeline generation tactic, with structured discovery conversations converting attendees into pipeline. Natalie Taylor (Episode #306) recommended structuring dinner events with embedded discovery conversations to drive post-event pipeline, aiming for 50%+ of attendees to express interest in a demo by the end of the event. Dave Gerhardt (Episode #214) described intimate dinners (2 customers + 10 prospects) as a "non-sexy but highly effective tactic for pipeline building" that scales better than large events.

Position B — Trade shows are better for new pipeline: Kera Wright (Episode #124) explicitly stated that trade shows (not hosted events) are the primary vehicle for generating new qualified pipeline from cold prospects, because attendees are already in a transactional mindset and expect to learn about products. Priscilla Barolo (Episode #302) recommended a mix of major trade shows, alliance partner events, and company-hosted roadshows for physical product marketing, with trade shows as a core component for reaching customers who need to touch the product.

Context dependency: Kera Wright's position may apply more to companies without an established brand or customer base to leverage for intimate events. The intimate-event advocates may be speaking more to companies with existing customer relationships they can use as social proof. However, both camps are making claims about pipeline generation quality that genuinely conflict.

Trend note: The intimate-event advocates are more recent (2024-2025) while Kera Wright's trade-show-first position is from early 2024, potentially reflecting a broader shift toward relationship-based pipeline generation over transactional trade show presence.

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4. Should webinars be gated (requiring registration) or ungated to maximize reach?

Support summary: 2 (gated/incentivized) vs. 1 (ungated)

Position A — Use gating and "attend to receive" incentives: Jay Schwedelson (Episode #329) cited data showing "attend to receive" incentives increase show rates by over 30% and drive 4x higher pipeline conversion vs. on-demand viewing. This approach requires gating and tracking live attendance to trigger the incentive. Matt Carnevale (Episode #155) recommended offering tangible incentives (free lunch, swag, tickets) to the first N registrants to boost registration and attendance rates, implying a gated/registration-required model.

Position B — Ungate webinars to maximize reach and build trust: Eoin Clancy (Episode #326) explicitly recommended removing gating from webinars to maximize attendance, focusing on delivering genuine value rather than lead capture, and measuring success through engagement metrics and 30-90 day pipeline influence.

Context dependency: Eoin Clancy may be speaking about a more mature brand with existing audience trust, while Jay Schwedelson's approach may be more applicable to companies still building their webinar audience. However, both are making general claims about webinar strategy that conflict on the fundamental question of whether to gate and optimize for live attendance vs. maximize reach through ungating.

Trend note: Both positions appeared nearly simultaneously (Eoin Clancy, ep. 326, Feb 2026; Jay Schwedelson, ep. 329, Feb 2026), so no clear chronological trend.

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5. Should you keep events small and focused, or go big at a small number of marquee conferences?

Support summary: 3 (keep small / avoid half-measures) vs. 1 (go big at few)

Position A — Keep events small and avoid half-measures: Jason Lemkin (Episodes #207 and #142) argued from direct experience running SaaStr that large events require union labor, vendor management, and enormous logistics overhead. Events rarely generate meaningful profit at scale and distract leadership. He recommended keeping hosted events under 200-300 people. Stephanie Christensen (Episode #227) makes a related but distinct point: if you do host a flagship conference, ensure you can fill at least 500 seats — a half-empty large event is worse than not hosting at all. Both positions argue against half-measures, but from different angles: Lemkin says don't scale beyond what you can manage operationally; Christensen says don't host a large event unless you can fill it.

Position B — Go big at a few marquee events: Mychelle Mollot (Episode #182) recommended choosing a small number of marquee conferences where you can make a significant impact and skipping others entirely, concentrating resources for maximum visibility and brand impact.

Context dependency: Jason Lemkin is speaking from the perspective of a company that runs events as a business model (SaaStr), while Mychelle Mollot is speaking about a company attending/sponsoring third-party events. However, both are making claims about resource allocation and event scale that apply broadly to B2B marketers deciding how to invest in events.

Trend note: No clear chronological trend identified.

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What NOT To Do

• Don't move too quickly into event execution without strategic planning. Packing the event program too full without thinking end-to-end wastes budget and misaligns with business goals. (Source: Stephanie Christensen, Episode #227)

• Don't treat all webinar leads as equal. Define your goal first—database growth vs. product sales—and choose topics accordingly. Treating top-funnel and mid-funnel webinar leads the same leads to misaligned follow-up and wasted effort. (Source: Jay Schwedelson, Episode #329)

• Don't host a flagship customer conference if you can't fill it. A half-empty event damages brand perception more than not hosting at all. (Source: Stephanie Christensen, Episode #227)

• Don't scale events as a primary revenue stream. Large events (1000+ people) require enormous operational overhead, distract leadership, and often lose money despite high sponsorship revenue. (Source: Jason Lemkin, Episodes #207 and #142)

• Don't measure brand-focused events by immediate pipeline. Brand events should be measured by awareness, pitch testing, and prospect engagement. Misaligning metrics with event purpose creates false negatives and kills valuable programs. (Source: Holly Xiao, Episode #270)

• Don't invest in experiential activations before validating the channel with measurable campaigns. First prove ROI with quantifiable campaigns, then invest in longer-term relationship and event activations. (Source: Brianna Doe, Episode #305)

• Don't send only marketing and events staff to conferences. Bring demand gen, operations, product, and other functions so they can directly observe customer language and market dynamics. (Source: Sandra Rand, Episode #265)

• Don't bury "attend to receive" incentives in webinar marketing. The incentive must be front-and-center in all marketing materials to drive the show rate lift. (Source: Jay Schwedelson, Episode #329)

• Don't wait until the next day to follow up on event leads. Drop leads into your CRM and send initial follow-up the same night of the event. (Source: Sydney Sloan, Episode #289)

• Don't spread event budget thin across many conferences where you can't make an impact. Either commit significant resources to a small number of events or skip them entirely. (Source: Mychelle Mollot, Episode #182)

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Sources

Episode	Guest	Date
#119	Peep Laja	2024-02-22
#124	Kera Wright	2024-03-14
#142	Jason Lemkin	2024-05-20
#155	Matt Carnevale	2024-07-04
#162	Natalie Taylor	2024-07-29
#174	Jared Fuller	2024-09-09
#175	Ruth Zive	2024-09-12
#182	Mychelle Mollot	2024-10-07
#183	Madhav Bhandari	2024-10-10
#189	Dave Gerhardt	2024-10-31
#191	Pranav Piyush	2024-11-07
#193	Priscilla Barolo	2024-11-14
#195	Andrew Davies	2024-11-21
#203	Gurdeep Dhillon	2024-12-19
#205	Amanda Natividad	2024-12-26
#206	Kyle Coleman	2024-12-30
#207	Jason Lemkin	2025-01-02
#212	Michael Cole	2025-01-21
#214	Dave Gerhardt	2025-01-27
#227	Stephanie Christensen	2025-03-13
#227	Kristina DeBrito	2025-03-13
#254	Kira Federer	2025-06-12
#255	Kelly Hopping	2025-06-16
#257	Kieran Flanagan	2025-06-23
#263	Jason Lyman	2025-07-10
#265	Sandra Rand	2025-07-17
#270	Holly Xiao	2025-08-04
#280	Gurdeep Dhillon	2025-09-08
#289	Sydney Sloan	2025-10-09
#294	Dave Gerhardt	2025-10-16
#302	Priscilla Barolo	2025-11-10
#305	Brianna Doe	2025-11-20
#306	Natalie Taylor	2025-11-24
#311	Dave Gerhardt	2025-12-11
#318	Kieran Flanagan	2026-01-05
#326	Eoin Clancy	2026-02-04
#329	Jay Schwedelson	2026-02-12
#332	Domi de Saint-Exupéry	2026-02-23
#341	Tess Pfeifle	2026-03-28