Seasonal Event Scheduling

I've spent $50,000 USD on flying out our 14 fully-remote team members to our 1-week offsite in Mallorca, Spain. Here's what we'll do, how I think about ROI (as CEO), and some lessons learned on running a fun AND productive offsite: Some context: - Grafbase is a fully remote team and we never had a physical office. - Our team is (literally) spread across the world. The furthest team members are flying in from Texas and Ohio. - We already hosted 2 offsites (Stockholm 2022, Barcelona 2023), so this is our 3rd one. Here's the FULL agenda: Monday: Kick-off with introductions, discuss what's working/not working, and brainstorm on a strategic topic Tuesday: Full day of FUN activities (windsurfing, paddle boarding, jet skiing) Wednesday: Work sessions, Separate group into small teams to build and present something tied to our 6-12 month roadmap Thursday: Another full fun-day, ending with a sunset boat ride Friday: Wrap-up, goodbyes and departures The ROI of all that? As the CEO, I see the energy boost lasting at least six months. There's less conflict, more empathy, and an upbeat vibe. It's also crucial for new team members and strengthens bonds. A happy team makes better decisions and is more creative. In fact, some of our *best* features and ideas were born during an offsite: - Open-sourcing our product (Barcelona 2023) - GraphQL Federation (Stockholm 2022, implemented in 2023) - Integrations with Datadog and other tools (Barcelona 2023) Here's what I learned about hosting GREAT retreats: 1. Choose a remote location to keep the team focused on bonding. Too much hassle can be distracting, we learned that from our Barcelona offsite. 2. Aim for at least 50% fun activities. This is key for creating bonds within the team. And work sessions should all be collaborative and enjoyable. 3. Fine-tune the balance between structure and free time. Too much work can be draining, too little structure might mean wasted opportunities. TAKEAWAY $50k/year for this retreat is a bargain compared to office costs in San Francisco ($120-240k/yr). Plus, the team building and creative output we get is invaluable. But it’s not a cost-saving thing. I’m investing in my team’s energy, creativity, and their bonds. My biggest note to self: The difference in team dynamics before and after meeting in-person is huge. Remote work has its perks, but yearly offsites are a necessity to make it work. Agree? Disagree?

CEO or CFO: “Is this event really worth us spending $20K?” Marketing/Comms/Sales lead: “I really think so… it’s in [insert cool city], so it’ll be great for morale and culture either way!” Yeah. That’s really not gonna cut it anymore. Budgets are tighter. ROI expectations are much higher. And “it’s in Napa” isn’t a business case. Here’s the real decision framework I use with clients to decide whether a conference, symposium, or sponsorship is worth it — before anyone books a single flight or hotel. 1️⃣ Clients and Customers If your current clients expect to see you there, that’s great. But show up with a real plan, not just a lanyard. A 30-minute coffee with a top client > three generic panels combined. 2️⃣ Prospects Will actual decision-makers (not “Business Development Associates”) be there? If not, it’s not a growth event — it’s a vacation in disguise. 3️⃣ Media Value CES, HLTH, Davos, JP Morgan, = tier 1 press magnets. Other have decent value for trade press. Most others? Not so much. If there’s no chance for earned coverage, deskside interviews, or content leverage, rethink the spend. 4️⃣ The $20K Question Flights + hotels + sponsorships add up fast. Ask: “What would this same money buy in paid, owned, or earned media instead?” What would it buy in recruiting and retention? 5️⃣ Location, Location… ROI? There’s a world of difference between Orlando and Singapore. If it’s overseas, it better be because your market or investors are too. 6️⃣ Launchpad or Lull? Announcing a major product, partnership, or data release? Then yes, the stage might be worth it — but only with real prep and a comms plan, not a last-minute deck. 7️⃣ Competitive FOMO If your competitors are sponsoring, don’t reflexively follow. If your customers aren’t there, let the competitors waste their budgets. If they are there, remember my rule: you’re either at the table or on the menu. 8️⃣ Thought Leadership vs. Thought Decoration Being “on a panel” isn’t thought leadership. If it doesn’t build credibility, create content, or advance policy or sales, it’s ego spend. 9️⃣ Life ROI If it means missing your big kid’s recital, sports championship game, or a big nonprofit board meeting, consider skipping it. No award ribbon for most frequent flier. ⸻ The best conference strategies balance impact, influence, budget, and time. Done right, they accelerate relationships and reputation. Done wrong, they just drain both. 👉 What’s your first filter when deciding whether a conference is worth it? (And yes, if you want to build an internal decision matrix or stakeholder map before 2026 conference season, hit me up. Happy Saturday, now time for a workout.

I showed up late to a Pavilion dinner and they made me sing ‘Sweet Child O’ Mine’ on the spot—awkward, but it drove $327K in pipeline. Our team is heading to SaaStr & Gartner CSO. Here’s our No-Booth Pipeline Playbook: 1. List First, Luck Later Don’t come in blind. Research every attendee, speaker, and sponsor name. Enrich against your ICP. Run list in ChatGPT: “Give me 1-3 convo points I can build my value around”. Now you’re armed with a list and thoughtful ice‑breakers tied to their business. 2. Lock Slots Pre‑Flight Two weeks out, DM prospects, clients, and people you want to meet—now you have an easy start to warm you up with pre-booked meetings during the event. 3. Just Have Fun Convos People overthink it: “How will I start a chat?”, “Am I bothering them at lunch?”. Get out of your head! Everyone there is looking to connect. Just go and talk to them, compliment their red Nikes, ask for guidance, or just say hi. What’s next? They come ‘inbound’ and ask “so what do you do?”—that’s it. Easy. 4. Go Where the Crowd Goes Don’t lurk at empty barista lines or charging spots. Go where people go. At sessions, talk with the folks sitting next to you—the talks offer great topics to discuss. During breaks, lunch/coffee lines will allow more casual talks. 5. The Real Event = Afterhours VIP dinners, breakfasts, parties, cocktail hours—this is where the magic happens. It’s where people have real connections, are less stressed, and build real trust. My karaoke moment at dinner turned into a long night of networking with our ICP, which continued to late-night parties and post-event follow-ups. People buy from people who share Uber rides, not booth swag. 6. Nail Your Talk Track Don’t wait until day 2 to feel comfortable with your conversations. Write down your qualifying questions, short, casual pitch, and booking process. 7. Book Follow-Ups on the Spot This is where ROI often gets flushed down the toilet. People try to play the volume game, but if you’re just collecting emails—prepare to get ghosted. Have meaningful conversations, make them memorable, and book on the spot! The best event follow-up is no follow-up; We pull our Chili Piper + Take notes over a screenshot of their LI profile + DM on the spot, “Great chat!” + Send Aligned room to stay top of mind, prevent no shows, and capture buying signals. 8. Mind the Little Things - Don’t look at badges (it’s like “are you a DM?”) - Don’t disqualify titles (title ≠ influence) - Don’t wear what won’t last the day (i.e. full wool suit) - Don’t skip breakfast, or sleep (or drink too much) - Don’t forget water (and Tic Tac :) —— A neon booth: $100K. Uber to dinner: $18. There’s more than one way to attend events. What’s your wildest zero-booth win or best tip? Best story earns a karaoke duet at SaaStr 🎤 See you in San Mateo & Vegas.

How easy is it to run an event? Anyone can put on an event but it takes professionalism to run one wel, and mastery to run one flawlessly. CORRECT POSITIONING When Melinda Palomino was scouting venues for her recent wellbeing retreat, she was clear the space had to reflect the We Are Lasenda brand and the premium positioning of her retreats. In a market full of low‑ and mid‑tier wellness options, the venue is more than a backdrop, it’s a key part of the proposition. Shangri‑La The Shard worked because it felt like an ascension above the world below, and the rooms themselves gave people what many events don’t i.e. enough space to feel calm, relaxed and free to move. The content matched the ‘container’, with carefully curated speakers and modalities that were emotionally engaging, intellectually interesting and genuinely useful, rather than a random line‑up of “names”. EXECUTION Execution is where it can so often fall down for live events and it’s what tied all the perfectly laid plans together. Laura Rosinska and the events team delivered a complex agenda with tight timing, multiple room flips and several transitions between spaces, whilst still preserving time for networking, rest and reflection. This type of flow doesn’t all happen by accident. Too often people “put on an event” and hope it magically comes together. However, events are live systems with lots of moving parts and even more humans with all their individual demands and foibles. Great event management – from venue choice to content design to on‑the‑day delivery – takes time, effort and meticulous planning. There’s a reason it sits near the top of the Forbes most stressful jobs lists. When events are done this well, what people remember is how easy it felt to be there. That ease is the product of real mastery. Congrats to all. #events #eventprofs #wellbeing #positioning

Here’s a mistake I see a lot of companies make before a trade show.  They try to be everything to everyone. They walk into a show with a generic elevator pitch.  They hope people will just “get” what they do.  They use broad language to sound more flexible.  And then they wonder why no one remembers them. Let me tell you what works instead.  Pick one clear ICP for that show.  One message.  One problem you solve that matters most to that audience. If your ideal client at this event is operations leaders at mid-market manufacturers,  everything you say should speak directly to what keeps them up at night.  If your target is packaging decision-makers, your talk track should make them feel like you’ve been sitting in on their team meetings. The goal is not to prove you can help anyone.  It’s to become unforgettable to the right ones. You want someone to leave your booth and say,  “That’s the team that gets us. That’s who we need to talk to.” Not,  “What did they do again?” This is how you move from being seen… to being remembered.  From talking… to converting. Start with your ICP.  Then shape your message.  Then train your team to deliver it with clarity and confidence. That’s how you make a trade show worth it. If your team is prepping for a fall show and the messaging still feels fuzzy, this is something I help sales leaders tighten.    Getting crystal clear on who you’re speaking to and what you’re saying can change everything. 

Dear Office of the CEO: a bad C-suite retreat can cost you upwards of $100,000 in wasted time, poor decisions and leadership distrust. Here are 7 steps to plan, design and execute highly engaging leadership retreats for your C-suite: 𝟭. 𝗦𝗲𝘁 𝗰𝗹𝗲𝗮𝗿 𝗴𝗼𝗮𝗹𝘀 Set clear retreat goals and expectations to make sure you are getting maximum value out of high stakes retreats. For example, are you looking for better team collaboration or improved strategy? 𝟮. 𝗜𝗱𝗲𝗻𝘁𝗶𝗳𝘆 𝘀𝘁𝗮𝗸𝗲𝗵𝗼𝗹𝗱𝗲𝗿𝘀 Reduce the amount of stakeholders to keep the retreat at an intimate level. Consider inviting star performers or external advisors for guest appearances on focused topics like increasing emotional intelligence or incorporating AI into the workplace. 𝟯. 𝗖𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝗹𝗼𝗴𝗶𝘀𝘁𝗶𝗰𝘀 Assess your C-suite team’s preferences on retreat location and lodging. Make sure to book the venue and secure travel plans months in advance. You do not want to scramble the week before. 𝟰. 𝗖𝗿𝗲𝗮𝘁𝗲 𝗮 𝗺𝗮𝘀𝘁𝗲𝗿 𝘀𝗰𝗵𝗲𝗱𝘂𝗹𝗲 Source session ideas from your C-suite team. Create a master schedule with agendas and session goals. Break up intense working sessions with team bonding sessions, meals and special activities. If you do too many back to back workshops, your C-suite team might doze off. 𝟱. 𝗙𝗮𝗰𝗶𝗹𝗶𝘁𝗮𝘁𝗲 𝘀𝗲𝘀𝘀𝗶𝗼𝗻𝘀 Appoint a trusted facilitator or hire one to help you run these high stakes retreats. If not, assign meeting minutes and action tracking to your Chief of Staff or Executive Assistant. 𝟲. 𝗖𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝗳𝗼𝗹𝗹𝗼𝘄 𝘂𝗽 After the retreat has concluded, send a copy of all notes and actions to the group, as well as a  feedback survey. Your Chief of Staff or the Executive Assistant can follow up with individual C-suite leaders for complete accountability. 𝟳. 𝗥𝗲𝗽𝗼𝗿𝘁 𝗼𝘂𝘁𝗰𝗼𝗺𝗲𝘀 Did you hit your retreat goals? Share the results of your retreats with your C-suite team and selectively share headlines with your entire company. Make adjustments as necessary for future retreats. That’s it. Follow these 7 steps to deliver amazing retreats that boost C-suite collaboration and improve company strategy. === Like this post if it will help you plan and execute amazing C-suite retreats. Comment below with other leadership retreat best practices that you've used. Follow me, Mackenzie Lee, for more Office of the CEO content and an upcoming, industry-defining Office of the CEO Playbook.

8 mistakes we made running retreats for 100+ people. So you don’t have to! If you’ve ever organised a large retreat, you’ll know: ➡️ What looks seamless on the outside often comes from plenty of hard lessons behind the scenes. Here are some of the biggest mistakes we made scaling up, and what we learned along the way: 1. Not budgeting for last-minute changes Build in extra time and money to adapt. 2. Not accounting for downtime Include optional free periods, nature walks, or quiet areas. 3. Underestimating logistics Plan with more margin than you think you’ll need. 4. Skipping on defining clear roles Assign team leads for logistics, food, tech, and content. 5. Underestimating catering needs Always triple check numbers to make sure there’s enough food, and label options clearly. 6. Not planning for waste management We now design all retreats as no-waste events, it’s better for the planet and for our community values. 7. Failing to clearly define goals Set 2-3 measurable objectives for the retreat to keep people focused. 8. Forgetting about post-retreat follow-up Plan post-retreat check-ins, shared notes, and actionable takeaways. For me, the deeper lesson is this: ➡️ As well as scaling numbers, you need to scale care, attention and intention. If you’ve ever planned a large retreat, I’d love to hear, what would you add to this list? ♻️ Share these lessons with your network ➕ Follow Maya Knight for more reflections on team offsites and culture

We spend ~$1M/year on trade shows and conferences. At first it was a giant waste of money, but now it’s a massive revenue driver for our business. Learn from the 8 mistakes we made early on to increase ROI at these events👇 1 - Engage Current Customers Logo retention & upsells lead to NRR & that’s as good as new revenue. Don’t shy away from opportunities to meet/engage customers. All current customers of ours sign the “do the work” board committing to another year working together to do the work. 2 - Have a Plan and Track All Metrics I mean it, track all metrics and know ahead of time what success looks like. It’s easy to come back from a show feeling energized, but your goal is ROI not energy. Track all customer/prospect interactions for post show attribution modeling 3 - Have a Meeting Space Biz dev deals get done after hours. It usually starts w/ someone passing by your booth, then ends meeting w/ someone after hours. At many of these shows there are no private meeting rooms. Having an extra empty suite to meet is key for biz dev. 4 - Have a Theme As cliche as it sounds, you need a hook to bring people to your booth. We’ve done everything from Elvis to a Beat The Box stores campaign. Regardless of the theme, we found that having a theme always beats not having anything to remember. 5 - Write Notes on Business Cards You’re going to be trading a lot of business cards, many times in quick convos. Carry a pen with you everywhere you go and write quick notes on the back of business cards you get to save in your CRM later. I promise you’ll thank me later 6 - Build Culture We are 100% remote, and conferences are the only time our team meets in person. Leverage this. Go a day early to strategize for the quarter. Go to a team dinner. And talk to someone you don’t see on Zoom. Take advantage of the in person time with the team 7 - Do a Retro After each show do a retro with the team that went and the team that helped execute everything. You can always do some things better / differently and some of the best ideas are from those that participated at the show for the first time. 8 - Host Your Own The single biggest revenue driver for us, is when we host our own show FloorCon. I’ll save the details for another another thread BUT I would recommend having the show near where most your employees live. Employees = show staff which saves tons of expenses

𝗕𝗮𝗯𝘂: How much did you spend on Dreamforce booth? 𝗙𝗼𝘂𝗻𝗱𝗲𝗿: $50k 𝗕𝗮𝗯𝘂: How much pipeline did you generate? 𝗙𝗼𝘂𝗻𝗱𝗲𝗿: We scanned 300 badges. 𝗕𝗮𝗯𝘂: How many converted in Qualified leads?  𝗙𝗼𝘂𝗻𝗱𝗲𝗿: 3 That's not Event ROI. That's stupidity. And that's also 9 in 10 booth exhibitors. Events have become SaaS startups' new way to burn cash, generate 0 revenue, and call it "branding". I spent last year traveling to events in Australia, Singapore, Malaysia, Dubai and Taiwan. Here's how to approach events with an ROI mindset: 𝟭. 𝗦𝗵𝗶𝗽 𝘁𝗵𝗲 𝘀𝘄𝗮𝗴: Everyone carries swag in luggage to save money. Because Shipping costs > flight baggage costs. The real cost, though, is babysitting your swag from airport → hotel → exhibit → booth. Salespeople at events should only care about Conversations & Pipeline. Not the dent on your standee. 𝟮. 𝗟𝗮𝗯𝗲𝗹 𝘁𝗵𝗲 𝗮𝘂𝗱𝗶𝗲𝗻𝗰𝗲: Old events were simple - exhibitors met buyers. Today, footfall has competitors, wannabe experts, influencers, sellers, random folks, & then actual buyers. These 2 in 10 real buyers are watchful and maintain distance. Identify them, and spend time talking to them. Not with freeloaders. 𝟯. 𝗬𝗼𝘂𝗿 𝗯𝗼𝗼𝘁𝗵 𝘁𝗲𝗮𝗺: Ideal size is 3-4. One bubbly personality who attracts audience. One SME conducting demos and talking tech. One salesperson who's NOT selling but taking notes, booking meetings. Fourth if possible - ops person handling logistics so the 3 can focus. 𝟰. 𝗟𝗲𝗮𝗱 𝘀𝗰𝗮𝗻𝘀 ❌: We generated $300k pipeline in 2 days with ZERO scans. How? Identify real buyers, have genuine conversations. My neighbour booths were busy scanning 150 random leads. I was making Qualified leads - book meetings on my calendar - on my laptop - at the booth. 𝟱. 𝗕𝗼𝗼𝘁𝗵 𝗺𝗮𝗴𝗻𝗲𝘁: 99/100 booths look identical. Nobody cares about your brand's color scheme. Think of a creative booth magnets -sth that gets the inner child of people out. We did a live superhero photobooth - teachers became superheroes, gave their emails in exchange for photo. 𝟲. 𝗣𝗮𝗿𝘁𝗻𝗲𝗿 𝗰𝗼𝗹𝗹𝗮𝗯: Invite a customer/partner/thought leader for a 30-min live demo at your booth. Their brand drives traffic at your booth. Pay them in Amazon vouchers or LinkedIn shoutouts. Best hack to engage with real buyers at scale. 𝟳. 𝗚𝗿𝗼𝘄𝘁𝗵 𝗵𝗮𝗰𝗸𝘀: Someone should ALWAYS be at booth (split lunch). Walk around, see what's working for others. Talk to competitors and collect intel. Think of clever magnets to attract audience (spin the wheel / lead scan for ice creams). Maintain booth hygiene at all times. 𝟴. 𝗔𝗜 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴: Every conversation can have automated meeting notes, logged in CRM, emailed to lead within minutes from the booth itself. Qualification AI agents tell you lead quality based on ICP. Another agent gives guided answers to tough questions. AI + humans = mad combo on booth. Events don't fail. Your event strategy does. Fix the strategy, fix the ROI.