Kailey Raymond

Top H1 takeaway from QBR's about our Rev Org: "We're an ecosystem, not a hierarchy." (h/t Alexandra B.) We collaborate, everyone's voice matters, and we strive to put people in roles they love so they can be madly successful. Hearing this statement was validation that what we are building in the Revenue Org at LibraryPass is unique, and scalable, and contagious. And we have roles coming soon! So if you're interested in being part of an ecosystem, let's chat. Here's to an even better H2!

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I distilled 𝟭𝟯+ 𝘆𝗲𝗮𝗿𝘀 of my go-to-market experience as a CMO/VP/Head of Product into this 𝘁𝗲𝗺𝗽𝗹𝗮𝘁𝗲👇 So, if you need help building a go-to-market plan, this resource is for you. I originally built this for myself for my consultation work. → I wanted a template that covered all of the key considerations in an effective and efficient go-to-market engine. → While also still being lightweight enough to be completed quickly (and no more than ~2 pages if printed out). Here's a summary of what the template covers: 𝗣𝗮𝗿𝘁 𝟭 - 𝗬𝗼𝘂𝗿 𝗖𝗼𝗺𝗽𝗮𝗻𝘆 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆 • 𝗠𝗮𝗻𝗶𝗳𝗲𝘀𝘁𝗼 - what you stand for, the change you're championing, why you should be trusted • 𝗣𝗿𝗼𝗱𝘂𝗰𝘁 - the urgent & important problem you're solving and how you're solving it better than alternatives • 𝗧𝗮𝗿𝗴𝗲𝘁 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 - segments, ICP and buying committee 𝗣𝗮𝗿𝘁 𝟮 - 𝗬𝗼𝘂𝗿 𝗕𝘂𝘆𝗲𝗿'𝘀 𝗣𝘀𝘆𝗰𝗵𝗼𝗹𝗼𝗴𝘆 • 𝗪𝗵𝘆 𝘁𝗵𝗲𝘆'𝗹𝗹 𝗯𝘂𝘆 - jobs to be done, buying triggers • 𝗪𝗵𝘆 𝘁𝗵𝗲𝘆 𝘄𝗼𝗻'𝘁 𝗯𝘂𝘆 - objections, fears, alternatives • 𝗖𝗵𝗮𝗻𝗻𝗲𝗹𝘀 they trust - where they learn and make decisions 𝗣𝗮𝗿𝘁 𝟯 - 𝗣𝗼𝘀𝗶𝘁𝗶𝗼𝗻𝗶𝗻𝗴, 𝗠𝗲𝘀𝘀𝗮𝗴𝗶𝗻𝗴 & 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 • 𝗣𝗼𝘀𝗶𝘁𝗶𝗼𝗻𝗶𝗻𝗴 and 𝗺𝗲𝘀𝘀𝗮𝗴𝗶𝗻𝗴 - per customer segment • 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 strategy - how you price vs the market 𝗣𝗮𝗿𝘁 𝟰 - 𝗚𝗼-𝗧𝗼-𝗠𝗮𝗿𝗸𝗲𝘁 𝗙𝘂𝗻𝗻𝗲𝗹 • GTM 𝗠𝗼𝘁𝗶𝗼𝗻 - sales-led, PLG, etc. • 𝗛𝗼𝘄 𝗪𝗲'𝗹𝗹 𝗪𝗶𝗻 - one sentence statement uniting GTM teams • 𝗗𝗲𝗺𝗮𝗻𝗱 Gen - how you'll generate demand • 𝗟𝗲𝗮𝗱 𝗚𝗲𝗻 - how you'll collect demand • 𝗦𝗮𝗹𝗲𝘀 - how you'll prospect, nurture and close • 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 - how you'll grow revenue 𝗣𝗮𝗿𝘁 𝟱 - 𝗠𝗲𝗮𝘀𝘂𝗿𝗲𝘀 𝗼𝗳 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 • 𝗢𝗯𝗷𝗲𝗰𝘁𝗶𝘃𝗲𝘀, 𝗧𝗮𝗿𝗴𝗲𝘁𝘀 and 𝗞𝗲𝘆 𝗥𝗲𝘀𝘂𝗹𝘁𝘀 - for Product, Marketing, Sales and CS As I said, it is comprehensive. But as you can see below, it's all done in a lean package. ___ Want the FREE template? 👉 The 𝘁𝗲𝗺𝗽𝗹𝗮𝘁𝗲 𝗰𝗼𝗺𝗲𝘀 𝘄𝗶𝘁𝗵 𝗮𝗻 𝗲𝘅𝗮𝗺𝗽𝗹𝗲 using a fictional company to help guide you through it. 1. CONNECT with me    ❗don't miss this step, I can't send you the post without :) ❗ 2. LIKE this post 3. COMMENT "GTM" And I'll share it straight with you :) Plus all my future training videos on it. ___ So why am I doing this? → Help better define what a GTM strategy consists of → Help others get a head start building theirs → Get your feedback to make the template better :) So what are you waiting for? ___ ✍️ Connect with me, like the post and comment "GTM" to get the template. ♻️ Reshare if you found valuable. #B2B #B2BMarketing #B2BMarketingStrategy #GoToMarket #Marketing #SaaS #Enterprise #BrandAwareness #DemandGen #LeadGen  #Sales #Data #ROI

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"There was a time when buyers were less incredulous about the decisions that they were making. Buying committees weren’t as large as they are now. Now sales and transactions are under a microscope." - Chris Turner, Sales Engineering Manager at @Salesloft On this episode of RevTalks, Chris and Rebby John, discuss changes to the sales and presales professionals’ roles, the keys to multithreading ever-expanding buying groups, getting to ROI faster in conversations, the story of “how” in sales, AI, and more. Full episode here: https://lnkd.in/e_GBVqJV

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Hey all 👋 I could use some help from GTM leaders/saas folks... Who is the best *marketing leader/head of marketing* you've ever worked with? For context, we're looking to bring in a Head of Marketing here at Circle to join our GTM leadership team. We're currently approaching $25M in ARR and growing fast (~100% y-o-y). This marketing leader will help us continue to scale to $100M+ in ARR. I'm biased, of course — but this can truly be a career-defining opportunity for the right person. —You'll get to shape how we tell the story of *3* brand new products that we're bringing to market this year. —The product is fantastic. Our product/engineering teams are the best I've ever worked with. The customers are the best I've ever worked with. You have all the raw materials necessary to do truly great marketing. We're already growing fast. You'll just help us go faster. —There are lots of new channels and untapped opportunities to go after. So there's plenty of room to come in and make an immediate impact. —This role sits on our leadership team. It's a group of the highest potential GTM leaders I've ever worked with. And we're ready to truly invest in product marketing as a function. — There's LOTS of momentum in the business. Our leading indicators like pipeline, win rates, word-of-mouth, NPS, retention, etc. are all really strong and getting better week-over-week. If you know a truly great marketing leader - I'd love to connect with them. I'd be grateful if you could tag them below or shoot me a DM. And if no one comes to mind, I'd be grateful if you could share this post for a bit of reach. Thanks! 🙏 Here's the JD: https://lnkd.in/e5fzB7T6

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I caught up with a few excellent startup operators (also great friends) who are looking for work. They encountered one common problem in their previous roles: founder fit. Great founders are: → Strategic but also into the details → Deeply rooted in customer experience → Intense and somewhat maniacal And they know how to lead. It’s hard to find a founder with all of these traits. To my network, if you’re looking for world-class leaders at scaling sales and customer success teams, let me know.

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GTM Leaders: Own the Arena When reporting to the board, don’t sugarcoat anything. If things are tough, lead with the red. Boards respect transparency, not fluff. - Master your numbers - Own your challenges - Share insights from failures It’s not about perfection—it’s about showing you’re the right person for the job. Like Roosevelt said: "It’s not the critic who counts, but the one in the arena, marred by dust, sweat, and blood." - Be honest. Be prepared. Be the leader they need #Leadership #CareerAdvice #ProfessionalGrowth #CEO #BoardMeetings #ManInTheArena

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This may be a hot take, but IMHO the single biggest thing that can influence your likelihood of success as a CMO is the due diligence you due on the company BEFORE you accept the role. Over the last few years since joining Pavilion, I've been privy to countless conversations in our community Slack channels where marketing leaders share their frustrations as well as horror stories of toxic workplaces, bad bosses, and impossible situations where they are set up to fail. While there are many factors beyond a CMO's control that might result in this type of situation, the truth is that majority of them could have been uncovered with better due diligence during the application process. Yet so many candidates are afraid to ask the tough questions, and afraid to probe deeply into the data - especially in a tough hiring market where they NEED the job. I guess the question is, is it worth it to take a job where you'll be miserable and set up to fail? I learned this the hard way earlier in my career. Every time I had a role where I was miserable, or my tenure was short, I could trace it back to poor due diligence on my part. It's one of the reasons I'm grateful I found Pavilion. When I joined, I took CMO School and in the first session, Andrea Kayal pulled back the curtain on her due diligence process and shared the exact question set she uses when evaluating potential roles. What I learned is that I need to be evaluating potential employers with the same level of rigor that I approach forecasting and developing strategies once I'm in a role. That means gathering data on things like: ⭐ Customer health (GRR, NRR and NPS) ⭐ The team, culture and people (employee monthly attrition rate, Glassdoor reviews, etc.) ⭐ Growth opportunities (TAM, SAM) ⭐ Sales and marketing (bookings targets, sales cycle length, size of pipeline, close rates, marketing budget, etc.) ⭐ Business health (performance against targets, CAC by channel, LTV, payback period) ...and getting to know the CEO, SLT and board well enough to understand how they think about marketing and whether I'll have the resources and support I need to be successful. The beautiful thing about this approach is that it actually makes you a stronger candidate because it demonstrates to potential employers that you are serious, thorough, and data-driven, and you have high standards - all of which are traits that also make you a better CMO. My advice to anyone looking for their next role is to invest some time in building out a thorough due diligence process - - and then stick to it. Expect to be asked to sign an NDA as part of this process. And lastly, if a CEO is unwilling to share this type of information with you, or doesn't have the information.... well, that is its own type of red flag 🚩 What other due diligence would you add to my list above? #CMO #kathleenhq

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Guess what - it's Thursday! Only 1 more power play to go! Next Topic: How to Make Messaging Stick "I’ve seen messaging make or break a launch. One of my first big PMM projects taught me this: if your audience doesn’t feel the value, they won’t care about your product. Here’s a messaging Power Play: 1️⃣ Use your audience’s exact words—dig them out of reviews, surveys, or sales calls. 2️⃣ Focus on emotional drivers first. Logic supports the decision, but emotion drives it. 3️⃣ Test, test, and test again. Messaging is never ‘done.’ I once turned around a project just by rewording the headline —it tripled the click-through rate. What’s one messaging tweak that’s worked wonders for you? Let's hear some insights from the experts: Elizabeth Brigham Maggie Bean Yi Lin Pei Katie Gerard

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Awesome SaaStock workshops yesterday led by Kevin "KD" Dorsey on how he operationalizes his sales teams and keep them up to date, Rita Jhaveri on the importance of customer onboarding with a fun workshop (Team Monkey FTW!), and Jake Dunlap for new insights on creating a effective buying experience. My biggest take aways from the sessions were: Our buyers' environment is changing and how they buy is changing. Are your internal processes staying up to date to meet your buyers where they're at? At startups I think of my sales org processes within a constant loop -> What's our.... TAM -> SAM -> SOM -> ICP -> Buyer Persona -> Pain Points for said personas within the ICP -> Does our product solve those pains points -> relevant messaging for marketing + disco + demo -> win customer -> case studies -> renew -> apply case studies and stories to new business sales cycle -> repeat The challenge I hear often is that people don't know what their ICP should be and so everything after that falls flat. But why is this so hard to figure this out? It's going to sound ridiculously simple..but it's your industry tags. Read more on why and how to fix it in the comments below and if you’re attending SaaStock today let’s meet up! #saastockusa2024

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When you're not in the board room, you're always wondering, "What's going on in there?". I have now worked with seven companies where I'd regularly present to a board, a mixture of PE and VC-led, and it's almost always centered around a few key topics. If you're meeting your numbers: - what's your future forecast  - how are you going to continue to grow - how will you grow faster and more efficient  - update on money in the bank and spend If you're not meeting your numbers (along with the things I mentioned above): - what is your plan to turn things around and meet your numbers (this includes new logo, back-to-base sales, and churn reduction) - what resources can they offer to help - do you have the right players in the right seat This is an oversimplification because many nuances are at play, but this is generally it. While board meetings can be stressful, almost every board I've worked with wants to be helpful. Of course, their interest is, first and foremost, that the business is healthy and growing, so there's always that undertone, but overall, they want to help. After all, they are guardians of the investments they make on behalf of others and have to report back on their performance. Think of them like they are CSMs for their investors (the folks that give them money). They need to get a great return on the investment they made on their behalf.

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For any PMM having a hard time nailing messaging… Facts - There’s no ‘Don Draper’ moment where inspiration will strike in the middle of a meeting. The good news is you have everything you need. 1. Look at your wins. Find the last 6 months of closed/won deals in your CRM. Find the patterns, and talk to the AEs if you need to. Better yet go talk to the customers themselves. Why did they buy? What made them pick you? 2. Once you have a good sample, use your judgement and distill out 3-5 ‘winning use cases’. These are the foundational proof points of why you’re differentiated. And they’re real 3. Then build the top and bottom. Top = what’s the one unifying value prop across the winning use cases. Bottom = what’s the product capabilities that support those use cases 4. Document this, turn it into your first call deck, and your website nav + core pages Refine this every 6 months. Sales will love it, and customers will actually believe you #productmarketing #messaging

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As automation takes over more of our lives, real human connection is more important than ever if you want to stand out. Two quick examples: I'm hiring for an enterprise AE role and a BDR position at Gusto. These are high-paying roles where you get to work directly with C-suite execs at some of the biggest companies working with small and medium businesses. We've had hundreds of applicants over the past few months, and less than 5 have bothered to email me directly to say they're interested and make a pitch. Of those 5 who emailed me, I met with 4. My birthday was two months ago and as always I got 50+ emails from different service providers wishing me a happy birthday including Banana Republic, my dentist, my insurance provider, and an online watch store where I recently bought a replacement band. This is lazy, ineffective marketing. If your team is doing this it shows they're not putting any thought into their work. Lets make 2025 the year of real personal connections and thoughtfulness! My inbox will thank you.

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When my friend Christi Williams from Hubspot asked me to run a workshop for some Partnership Leaders on top ChatGPT use cases, I initially thought "do I have enough material for 1 hour?" Turns out, I could go on for hours* on the incredible ways you can leverage the tool, and some of the top use cases for partnering professionals we covered include: 1/ Copy writing (outbound to partners, prospect, proposals, etc) ▶ get to ~80% on your own and let GPT get you the rest of the way 2/ Data Analyses & Table Construction ▶ pump in CSVs/data files and query GPT to understand trends, takeaways ▶ not great with VLookUps? Just pump in a CSV with a table set up & ask GPT to produce a version complete with complex formulas 3/ Cross-functional collab. ▶ summarize long winded Slack threads to understand max content and what most important outstanding questions are ▶ translate your proposals into language tailored to Product, MKTG, Engineering, etc, and for international colleagues 4/ Call Review and FUPs ▶ take no notes on calls, just stay laser focused and rely on GPT to ask questions about the call and get key action items & drafted email FUPs/internal Slack messages 5/ Enablement ▶ Create custom GPTs trained up on your partner network and make this accessible to your frontline teams so they get accurate information ON DEMAND ▶ Do the same for partners; pin a GPT about your company/product in a Slack thread so your partners can get key info in real time I hope these examples are helpful; would love to hear how other GTM professionals are leveraging AI! #AI #ChatGPT #OpenAI #GTM

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A big thanks to AI guru Nicole Leffer for taking marketing leaders from Cervin Ventures' portfolio companies through her "Harnessing the Power of Gen AI for Marketing" seminar today. Every time hear Nicole speak I come away with a dozen new AI tips and tricks -- and she delivered again by showing us how to build foundational skills in our marketing orgs. I won't steal her magic but here are a couple of Nicole's context-setting observations: 🤖 AI is a great assistant, not a replacement for marketing. AI can't do ALL of your marketing, especially in these early days. (So don't even think about taking humans out of the loop yet.) 🤖 Marketers using AI think they are further along than what they really are -- mostly because they don't know what they don't know. (Good news, if you're incorporating AI into workflows, you're still ahead.) 🤖 AI and the models are currently the dumbest they will ever be. If you can do great things with them now, think about what they will be able to do in the next 3-5 years. Thanks to all the Cervin companies who participated! cc: Christine Vidal, Daniel Kish, Crystal Mendes, Josh Dreyfuss, Jeanette Belashov, Justin Mota, Marwa Mhtar, Kristi Tutt, Tyler Fridley, MBA, LingRaj Patil, Phoebe Wang, Ashley Daniels #marketing #ai

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Every company & every product has a name. Yet, few folks truly know how to name one. I’ve named companies and products for startups and big brands. I wrote a post this week about naming the Uber One subscription, and Paul A. responded with a request to write a post about the process. Challenge accepted! Let's start by saying that there are plenty of successful companies and products with bad names. Facebook (so lame), Spotify (what), and even Instagram (now everyone just calls it IG). But a good name is a tailwind. And building a business is all about generating tailwinds. Scrub Daddy - instantly makes it fun Shark - a vacuum that looks like a shark and a name you won’t forget Airbnb - fun and easy to remember—unlike VRBO Apple - for a computer! Love it Skims - so simple So, how do you name a company or product? Here are steps to a simple & comprehensive naming process. Step 1 - Brainstorm A well-structured brainstorm is key. You need the right people in the room, with the right prompts, in an environment comfortable enough for all ideas. The goal is to generate as many names as possible. This is a good opportunity to include stakeholders so they feel part of the input. Step 2 - Evalutation criteria Be specific about your needs, and exhaustive. Your criteria will generally have things like: Trademarking - can we own the trademark in our category? Domains available - if a company, what domains can we get? Internationalization - does this word have meanings in other languages? I recently heard about a startup named Corva, a very bad word for anyone who speaks a Slavic language. Don’t make this simple mistake! Alternate meanings - does this name have multiple meanings? Connotations test - Positive or negative connotations? Relatedness - does this communicate a key aspect of our product? Differentiated - how different is this from our competitors? Etc. Make sure your stakeholders approve the criteria! Your criteria will likely remove 90% of your ideas to help you filter. I recommend using a spreadsheet with your criteria as columns. This creates a simple tool to filter names by criteria easily. Step 3 - Picking a name The hardest part of the process is buy-in. Naming is more of an art than a science. I've generally used a voting process. Some tips: - Put the final names into a deck with the finalists used on the website, packaging, ads, etc., so your team can see it in situ. - DO NOT include the internal code name. It will always win the top votes as it is the most familiar. Even your smartest, most discerning colleagues will fall for the familiarity trap. I saw it at Uber many times. Step 4 - Sell it Unveil the name with a splash! We often did this by creating fun campaign examples with the new name. We made social media posts, billboards, and even ad campaigns to show the team how the name would bring their work to life. Happy naming!

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When I first joined Frontify and the partnership team, I quickly got used to using Gong for all my external calls. The funny thing is, more often than not, the people I'd speak to would also get very excited about it and ask if they could get it too (mind you, this was BEFORE the big AI hype). So naturally, when Udi Ledergor 🏳‍🌈 invited marketers to talk to him and learn more about how to leverage Gong for marketing, I was excited to hear more. While talking to Udi, I was reminded again about what a great tool Gong is (yes, I work for a SaaS company, and I love software, so what) and how easy it is to leverage for direct feedback at scale from your customers and prospects. Thanks so much for the insightful session, Udi!

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I’m curious - for revenue leaders out there: how are you thinking about outbound pipe gen roles? What title(s) and mix of skillsets have you found to be the most effective? I’m working with Nick Casale to build out our revenue org at AirOps, and we’re looking to hire a rockstar to own outbound pipe gen. Our ideal candidates: --> High IQ + EQ --> Scrappy and competitive --> Analytical + reasonably data savvy --> Can figure out new tools and automations (the emerging AI GTM stack) + excited to learn/master prompting --> Exceptional writer --> Not afraid to make a cold call (but won’t just be dialing for $'s) --> Motivated to own and crush a pipeline generation quota --> Wants to pursue a career in Sales or Growth If you or anyone you know fits the bill, DM me. The JD to apply is in the comments 👇

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Big takeaway from #gainsight #pulse2024: AI is going to free up CSM time to be “more strategic” I have heard some version of this 40+ times in 1 day. What does this actually mean though? I am asking because I really don’t know what people mean when they say “more strategic” I can hypothesize a lot, but I would like to hear from a broader group. What does it mean for CSMs to be “more strategic”? Also, what is the value to a business of CSMs being “more strategic”? Looking forward to hearing perspectives from others!

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"So make the friendship bracelets Take the moment and taste it You've got no reason to be afraid” 🎤 “You’re On Your Own Kid” by Taylor Swift One of the most common questions I get at Gainsight (beyond “why do you have so many shoes?”) is “what have you learned about running events?” Coming off the high of having 2000 members of the #CustomerSuccess community together with us in St. Louis last week at #Pulse2024, I thought I’d share 5 things I’ve learned over 11 years of Pulse events: 🎉 Create and Execute On a Bold “Fun” Theme: So many conferences are SOOOOO boring! A big chunk of the reason is the events lack a soul. For us, the formula that’s worked is to start with a cultural concept that evokes emotions. In this case, we made Pulse 2024 all about high school and the 1980s. We then had our design dream team, led by Hayley Cromwell, execute a stunning visual experience, including high school lockers, a Breakfast Club spoof and branded jean jackets! 💪🏾 Link the “Fun” Theme to a Business Theme: We juxtaposed the humanity of the past (1980s and high school) with a human and vulnerable look at the future. Everyone naturally has excitement and anxiety about the effect AI will have on humans. We announced what we called the “Human-First AI Playbook,” including dozens of AI-powered features in our product. ❤️ Lead With Vulnerability: As many of you know, I’m a fan of bringing vulnerability to business. This shows up at Pulse in many ways. One is me doing a closing keynote about my personal journey. This time, I shared a story about adversity and uncertainty (climbing out of the Grand Canyon after just tearing my ACL in the canyon) and what it means about understanding our own work and personal futures, particularly in the face of AI. I think opening up sets the tone for others being “real” with fellow attendees. 👊🏾 Build Community: Nothing brings me more joy than seeing the #CustomerSuccess community coming together - to help each other, give advice or be a shoulder to cry on. We try to reinforce the concept that “Pulse is not a Gainsight conference, it’s a community conference.” In the first keynote, we do our annual “Pulse fist bump” (find a neighbor and give them a fist bump). Symbols like this go a long way. 😂 Moms FTW: While Andy Cohen (our celebrity guest) was funny, no one could top my mom. Quite bizarrely, my mother has become a big part of the Pulse community and regularly has been featured in the keynote. Whether walking onto the stage to give me a fist bump and tell me “you forgot your lunch” or pitching Andy Cohen on a TV idea (see below), family help to humanize the experience of a business conference. While those are my learnings, the real stars of the show were our EPIC events team, led by Lauren Olerich and Kat Leong. Best in the business, my far! What have you learned from hosting events (whether big conferences or small dinners)?

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