Kailey Raymond

At Costanoa Ventures, we pride ourselves on identifying and supporting exceptional founders poised to create impactful, lasting change. Hona is a shining example, driven by a trio of extremely talented founders: Manny Griffiths, Joshua Christensen, and Matt McClellan. They each bring unique, differentiated expertise to the table, and Amy Cheetham and I are extremely excited to partner with them. There are approximately 450,000 law firms in the United States, with half of those firms being B2C - think personal injury, mass tort, or immigration law as opposed to BigLaw. One of the reasons we love how Hona is tackling this market is their focus on B2C law firms and product excellence - B2B firms are historically difficult to sell brand new software products into, but B2C firms are completely different buyers. Oftentimes there's just a handful of lawyers and paralegals in a partnership, and any piece of technology they can use to give them an edge would be valuable. 44% of negative Google reviews on law firms directly reference poor communication as the reason for a negative experience, and the number 1 reason for Attorney Bar complaints in the U.S. is "lack of communication". On the lawyer's side, attorneys, paralegals and legal assistants spend an average of 7.4 hours per week on unnecessary updates, redundant communication, and activities that aren't directly contributing towards getting a client's case solved. Manny and the team at Hona are working to change all of that. Hona delivers a tightly-integrated communications platform to help facilitate better communication between law firms and their clients. During legal proceedings, client communications tend to be a large resource-stressor for law firms. Clients will frequently call firms for case updates, legal explanations, or general administrative questions that tend to eat away at firm resources without providing any additional progress toward case resolution. Hona exists to ease that burden - it’s a platform that allows law firms to efficiently communicate with their clients over text, easily build customizable web pages and embed videos, and share information on case status and basic legal process education. This crucial communication processes allow attorneys to focus on their job – moving cases forward, while keeping their clients informed and educated. If you're a lawyer dealing with these problems - don't hesitate to reach out to us or the Hona team! It's a privilege to work with Hona on this journey. The company has been growing at a rapid pace, and they're delivering meaningful technology to help people get through legal proceedings in a much more fluid, transparent, and easy process. Manny, Joshua, and Matt are exceptional founders whose combined skills and dedication to continuous learning position them perfectly to lead Hona to success. They're just getting started, and we can't wait to see what they'll achieve.

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For my early career friends in strategy consulting

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If you're thinking about building a partner program, tiers can be a good idea. Partnership tiers motivate partners to sell more and move up to get access to more. One of the most common questions I get is - what should be included in the base tier and what should only be included in the higher-level tiers. Here's my framework of how to think about it. Anything that will help your partner sell more and faster, should be included in the base tier. Your goal is to help partners sell more and move up in tiers faster. I know this sounds simple, but so many companies don't include co-selling and co-marketing in their starting tier, which is a big mistake in my opinion. Why would you limit co-selling and co-marketing? Don't you want to help your partner sell more? I'd argue, that the higher the tier, the less your partner should need co-selling... In the same way, you include training in your base tier, make sure to include all the other things that will help your partners sell more and better.

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Join this discussion (bit.ly/3UljG3Z) to understand how to build a revenue process that's focused on buying rather than selling. Learn how to enable salespeople to run the process and founders to evangelize and bring gravitas.

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Curious about how to navigate the ever-changing influencer landscape? Join me tomorrow at Morning Brew's NYC event, "Perfecting Your Influencer IQ" where I'll be speaking with Mae Karwowski, Founder & CEO, Obviously & Kyle Hagge, Chief of Staff, Morning Brew about: 🌟 Consumer Sentiments: Understand the current attitudes and behaviors about influencers. 💡 Maximizing ROI: Strategies to leverage influencer partnerships effectively. 📈 Trends: Discuss the latest trends shaping the influencer landscape and how to stay ahead. It's not too late to register: https://lnkd.in/dwvaDSiZ #InfluencerMarketing #ROI #ConsumerInsights #MarketingTrends #MorningBrew

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A topic that comes up often with companies we work with is how they think about the (Return on Investment) ROI of group travel for offsites and retreats. I’m excited to share thoughts in partnership with the Chief of Staff network tomorrow at 12 pm EST. You san RSVP here: https://lu.ma/kstmwma6 Before considering the ROI, we should consider the investment itself. 1. Prior to COVID, companies paid for rent (duh). Many companies paid $1.5-2.5K+ per employee per month per rent - Companies didn’t have a choice on whether or not to pay for rent - A right of passage for startups used to be raising a seed round, and taking out an expensive lease - In cities like SF and NY, rent is expensive: $80-100 per sq ft. - Based on avg. sq ft per employee, and other expenses like snacks, security, etc. spend on rent adds up! 2. With distributed work, companies have to spend less on rent (sometimes a LOT less) - Some remote companies are spending nothing or very little on rent - Even for in-person companies, because employees aren’t coming in every day the sq footage needs are down - The price of commercial real estate has also fallen considerably - For example, all we spend on rent at Marco for a few WeWork subscriptions for certain team members 3. Companies are now spending more on T&E (offsites and onsites) - Spend on rent is lower, but spending on T&E has gone up - More employees are distributed, but the need for in-person connection hasn’t gone away - Many companies are now investing in gatherings 2-4x per year - On the whole, companies should be saving money between rent and T&E 4. With much lower spending on rent, and higher spending on group travel, on the whole companies should be saving a LOT I’ll break this math down, and show how we’ve seen companies measure the impact of gatherings like offsites tomorrow! #employeeexperience #offsites #futureofwork

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I could talk about product positioning all day. Good product positioning makes it easy for buyers to see themselves, their routines, and their goals reflected in what you're offering them. Sometimes it's shifting your product positioning from "what we do" to "what we do for you". What a dream getting to meet and talk with Daniel Murray of The Marketing Millennials podcast about: ➡ Creating product positioning that resonates (and how we think about it at Recharge ➡ Sustaining brands in the routine economy ➡ Why your first marketing hire should be a product marketer, and more Check out the full episode ✨

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Employee terminations: they're a topic no one wants to discuss but that every company has to navigate. Thankfully, Melanie Naranjo and wonderful Ethena advisor (& Gusto's former People Leader) Jess Yuen are tackling this tricky topic for the next Ethena webinar. Register if you want to learn more about these topics: How to pressure test whether or not termination is the right course of action Best practices for communicating termination decisions How to minimize risk and choose the best course of action when things get tricky Critical pitfalls to avoid

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I’m excited to share a new project: Estuary. It’s not for everybody. It’s a newsletter for ~100 people. They’re GTM leaders who: - want to diversify their sales & partnerships channels - are curious if VC and PE partnerships make sense for them - aren’t sure how to launch this bespoke strategy Being from Louisiana and now living in coastal North Carolina, Estuary brings to mind for me not only diverse ecosystems but also resiliency in the face of change. Sales orgs that thoughtfully experiment with new routes to market will win. My first few posts will focus on the basics, and we’ll move forward from there. The link to sign-up is below. I hope you’ll join me, and I hope you’ll tell your friends. #vc #pe #gtm #sales #saas #partnerships Photo: The Nature Conservancy

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📈 🎯 Hannah Leary is a revenue leader, technical customer practitioner, and discovery master. 🎯📈 It's W12 / Q2 / 2024 and this week in our MGMT Boston up & coming operator series we’ve got Hannah, who serves as the Founding AE at Boston based marketing technology startup OneScreen.ai, helping B2B and B2C companies spread their message from the digital sphere to the real world through out-of-home advertising. As the Founding AE, Hannah is doing anything and everything related to GTM. She is managing pipeline, purchasing software, helping to define their ICP, working on messaging, collaborating cross-functionally, creating processes, AND carrying a full quota! She spends a lot of her time collaborating closely with OneScreen co-founder & Chief Customer Officer Greg Wise, CEO Alex Ewing, and their media planning team. 💡 Deals are Closed During Discovery 💡 When Hannah became an AE, she sought to tailor a specific & better approach to discovery. Her impression was that proper discovery is rarely done and it’s become a passion. In Hannah’s view, there are three levels of discovery: 👤 The Contact - does the primary point of contact have the ability to make a decision? If not, who is and will they be a part of the buying process to better organize timelines? ⏳ The Deal - how is the buying decision being made? Who else is involved? What other approaches are being considered, why, and what steps have they taken already? How does that fit into the customer’s budget? 🚀 The Campaign - what is the customer actually looking for in terms of performance - in OneScreen’s case: who are they looking to advertise to - cities, areas / formats (and other tactical details) and can we deliver? 3 Career Insights / Learnings 🤝 Make Connections - “I’ve made some of my best friends and most important career connections through places I’ve worked. Networking and making connections can bring so many new opportunities if you commit to cultivating those relationships” 🙋‍♀️ Raise Your Hand - “You have to open yourself up to different opportunities to find out what you like and what fits your professional personality. Being able to get my hands on a bunch of different things allowed me to learn how much I love building early stage startups & teams with an influence in their strategic direction.” 🥂 Celebrate Your Wins - “When I started my career I never really knew if I was doing a great job unless I got praise or direct feedback. There is a whole qualitative aspect that goes into everyone’s role (especially Sales) and its important to me to celebrate daily wins to continue helping celebrate wins around me so that our sales team knows what factors will help us win outside of the numbers” If you’d like to learn more about Hannah’s career, the full post is linked in the comments. Go ahead and sign up for the newsletter to see the operator learnings we bring you in the weeks ahead too, will ya? #bostontech #operators

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How do you succeed as a marketing leader at a fast-growing startup? I sat down with Devon O'Rourke on Embracing Erosion to share more about my journey as marketing leader from pre-revenue to post Series D at Beamery. We covered off on a ton in this conversation, including... 🌱 How to build and scale a marketing team from the ground up 🔄 How to evolve your skills as a marketing leader, and the capabilities that are most important at every stage of growth 🔎How to find and develop world class talent 🤖 How to use technology and AI to hire based on potential vs past experience 💊 Why in difficult times it’s important for your product be perceived as a painkiller vs a vitamin (and how to evolve your positioning in line with this) You can find the episode wherever you get your podcasts. Give it a listen and let me know what you think. What are the strategies that have helped you find success as a marketing leader? #marketing 

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The second set of breakouts at Kickstart Fund CEO summit phenomenal featured Josh Duncan and Stan James discussing the nuts and bolts of SaaS GTM motion and Grant Gordon and Jeremy Hanks sharing their perspective after their exits - What did they learn? What would they do differently? Here are some takeaways from each: SaaS GTM 1. Setting a solid foundation early on is crucial, including knowing your numbers, focusing on a narrow market, and aligning your GTM functions. Establishing a culture of truth-telling and active listening is essential for driving performance and understanding customer needs. 2. Reframe proof of concepts as proof of value. Shift away from traditional proof of concepts and instead focus on demonstrating proof of value. When engaging with potential customers, clearly define the expected outcomes, timelines, and a path to a commercial contract. Perspective after an exit 1. Embrace the journey, not just the destination. Find fulfillment in the daily process of building a company, rather than solely focusing on the exit.  Establish a strong company culture. Culture isn't just a buzzword, but a crucial element for employee satisfaction and productivity. Deliberately shape and iterate on your company's culture, treating it as a product for their employees. 2. Set personal firewalls to protect your well-being. Establish boundaries to safeguard your mental, physical, and relationship health. Separate your identity from your role as a founder. Build a solid support system - an executive coach, fellow entrepreneurs, therapist, etc.-to help you navigate the challenges of the startup journey. 

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Consumer incentives and motivations are multi-faceted and complex. I find qualitative marketing frameworks for segmenting users by readiness to purchase and “persona” to be distracting and unproductive -- and, at worst, providing a thin veneer of rigor that gives a marketing team license to spend money with no accountability. In my view, the best approach to optimizing marketing spend for commercial outcomes is to anchor robust and exhaustive advertising experimentation with a reliable, quantitatively sound measurement framework that focuses on incrementality.

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Winning early GTM via founder led sales is an essential step in building a consequential start up. 🎯 But, while there are countless conferences focused on scaling GTM once you've hit a couple million in revenue, to date there hasn't been a conference focused on FOUNDER LED SALES and nailing the earliest days of GTM. 👀 😅 That ends now. 🙌 Pear VC has helped 100+ founders learn how to sell, how to build their 0-to-1 sales engine, how to get from $0 ARR to $1M ARR -- and now we're introducing the first ever GTM CONFERENCE for EARLY STAGE FOUNDERS. ⭐ "Zero to $1M: Winning Early GTM" will be held in San Francisco, CA this September 5th! ⭐ If you're at the idea 💡, pre-seed 🌰 , or seed stage 🌱 , this is the GTM conference for YOU. Come hear from Pear veterans, industry leaders, and successful repeat founders like Sanjit Biswas (Samsara and Cisco Meraki Co-founder and CEO), and leave with actionable guidance to supercharge your startup’s revenue from day 1. ​ ➡ APPLY NOW! Space is limited, and the early application deadline is July 15th. Pepe Agell and I will review applications on a rolling basis. 🚀 CANNOT WAIT TO SEE YOU THERE! 🚀 #earlystageGTM #zeroto1M #founderledsales

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🌶🌶 Category creation has been all the rage. 🌶🌶 Kyle Poyar's post from James Evans is gold on this topic. My TAKEAWAYS: 1️⃣ Category creation = playing the game on HARD mode 2️⃣ Before & after narratives = critical 3️⃣ Repositioning > Pivoting I feel like I've been waiting for years for someone to call out category creation like this. Category creation seems great. It sounds so bold. So "Blue Ocean." Very "Alpha." We don't play by other people's rules... we make up our own rules! But being so novel nobody "gets" what you are? That's hard. Hard for customers. Hard for investors, Hard for employees. If you loved the book "Play Bigger"—the latest darling of category creation—this is the counterpoint to round out the topic. Locally, Qualtrics was the poster child for category creation. They hired the authors of "Play Bigger." But “experience management?” Really? What does that even mean? Are they an app for travel agencies? When’s the last time you took a survey and felt like you were having an experience? Never made sense to me. ... also if you need further proof that I know what I'm talking about and that Qualtrics is up in the night...well, I’m still working for a living and Ryan Smith owns the Jazz after scratching $8 Billion on a napkin while playing basketball. 🤷🏼‍♂️ 😜 😱 Win some, lose some. P.S. IMHO, "Play Bigger" is an "also ran" to the O.G. and much more practical "Positioning: the Battle for Your Mind" Don't believe me? 🤔 Never heard of Positioning: the Battle for Your Mind? 😕 That's okay. FYI Play Bigger was a best seller with over 150,000 copies sold world wide. It only needs to sell 3,850,000 more copies to catch up to Positioning. 😁 #cmozen #positioning #categorycreation

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One awesome thing about our work at Groops is that the organizations who seek us out are the ones who care deeply about their people. Summer Friday is one of those companies. Culture is built into their core values and shapes everything they do. Every decision they make is grounded in how it impacts the human doing the work. I know because they have Groops for their entire company and I also lead their executive Groop. We have been with them for over a year now. We bring experts in organizational psychology to meet with their teams on a regular basis, teach core content in high cohesion / high performing teams, and help them have regular, honest conversations about what is working and what they want to improve. We provide ongoing insight reports with recommendations so everyone stays in communication. So, we end up knowing our partners well. They invited us to lead a full day (virtual) retreat last week where everyone took a personality assessment and we spent the day discussing how team makeup impacts their performance, how engaged they feel, and the direction of the organization. This is particularly important for them as they are a virtual company and clear communication and exploration and articulation of team functioning are mission critical. Having these types of conversations is also how cohesion is built. Bravo Summer Friday. We are proud to be your partner. Awesome work Rob Simone, Sarah Roberts, CPA, Michael Cruz, and Alicia Wiedemann. You are great leaders. And thanks Charlotte Bingaman MArch EdM , Sydney Davis, and Allison L. Barnes, MA, PCC. I am proud to have you on our team. #peoplematter #workplacewellness #peakperformance #IOPsychology #IOPsych #industrialorganizationalpsychology #cohesiveteams #connection

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Over the years I’ve seen the post going around in various forms of how Bessemer Venture Partners keeps a *robust* anti-portfolio on their website. It’s fun, self-aware, humbling, and differentiating. If you haven’t already, go have a look. (As an aside, I’ve been to their offices in Cambridge multiple times back in the day while visiting Kent Bennett, the venerable Felda Hardymon, my dear friend Steve Papa (if Steve was capable of “friendship”), and the young(er) founders of a company called Toast - Bessemer wallpapered their bathrooms with the rejection IRMs of said anti-portfolio). Anyone who has been in the game long enough probably has their own version. Companies they could have invested in, but passed on, only to be made a fool when said company later becomes a decacorn. My personal opinion - and I tend to think one that Bessemer shares - is 1) we all make mistakes, 2) we’re human and at times quite dumb, and 3) hell, at least we had access in the first place. Venture investing is about seeing as many amazing opportunities as you can, even if sometimes that means missing a few…dozen. Either that or I’m totally full of shit and we’re just plain idiots. What do I know. I’ve only been doing this for three years. ¯\_(ツ)_/¯ In any case, in the spirit of giving myself a Father’s Day gift of crow, which I plan to eat, here are some of mine: Toast: not sure if Steve P would have let me into his $4M or whatever it was round never mind the Seed or the A, but I feel like I could have convinced them. Steve F and Aman said they were going to fully rebuild a POS after running into integration nightmares with Micros, Aloha, et al, and I thought they were crazy. Old industry incumbents. Entrenched. Insert foot in mouth, and then pull it out and use it to kick my own ass. Klaviyo: TJ Mahoney was a pre-seed investor and he told me about it. Said AB was a stud. I passed without even talking to them. $8M valuation or around there I think. Shopify ecosystem play? Ew. Sigh. I’m a dumbass. Pillpack: mentored TJ a bit early when he was having some team stuff going on at Techstars. The hippie. $4M post or something. Said no. Whoops. Drizly: Nick Rellas kept stonewalling me, the little twerp, but pretty sure I had a small spot. Pat Kinsel would have got me in. Slept on it. Round closed. I’m an idiot. Draftkings: met Jason at a dinner and Ryan Moore told me to hop in at pre-seed - I already had a small play with a competitor. Jason and I became great friends (which we are to this day). Really knocked that one out of the park. Way to go, Phil! Good eye! Anyway, PLENTY more where that came from and I’m sure I’m currently in the process of creating one of the world’s most epic anti-portfolios at Impellent Ventures. But, again, c’est la vie. Better than sitting on the sidelines and wondering what could have been. At least I know what could have been - a gazillion more dollars than I have right now. Ah well. Batter up! *p.s. I’ve had some winners, too ;)

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Excellent and very practical guide from Aileen Allen. This will help a ton of founders. #marketing #startups

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👷‍♀️ Blink - The Frontline Experts is building a “super app” for frontline organizations to make working lives easier. 👷‍♂️ It's W8 / Q2 / 2024 & this week in our MGMT Boston startup series we’ve got Blink, a growth stage startup building a better workplace experience platform for desk based employees to connect with their deskless colleagues who spend their days out in the world, fixing our problems and servicing our needs - and traditionally are hard to reach. Blink is helping employers uplevel their internal cultural experience and help employers better understand how their disparate workers are thinking & feeling. In the U.S. there are more than 40M frontline workers with deskless workers encompassing 37% of the total workforce. These are employees in industries like healthcare, retail, manufacturing, higher education, utilities & transportation. Eighteen months ago they made the decision to expand from the UK to the US. Founder Sean Nolan moved to Boston and hired CRO Jim McInerny to build out the team. In the months since they’ve added local leadership like Sloan Kendall from Gainsight, Marcy Paterson from ServiceNow, and Amanda Haltmaier from HubSpot. Blink counts almost 20 employees locally here in Boston. In the coming quarters they plan to roll out their workforce insights & frontline intelligence product. AI generated questions will help dig into employee concerns and feed the insights back to HQ where executives can diagnose and solve turnover challenges. Blink is diligently co-developing these new features with current customers. In Boston they’re strong in the EMS sector so ambulance personnel at companies like Cataldo & Action Ambulance aren’t rushing back to the office after saving peoples lives to file paperwork! Even the MBTA is a customer. In 2023 Blink grew U.S. top line revenue by 159% and welcomed 52 new customers, now counting over 100 enterprise customers. In 2024 they will continue to focus on the U.S., its fastest growing market, planning to double the size of their U.S. headcount over the next 12 months. For Sean, Boston has been the best combination for a European founder - easy commutability home to the UK, time zone overlap, a great culture, and access to top talent as an Enterprise SaaS startup. And on a personal note,  it felt like a great place to raise a family building a startup for the long haul. Operators to Know (Locally): -Marina Addonizio, Senior CSM, Enterprise -Tanner Fogarty, Senior Enterprise Account Executive -Matt Haley, Account Executive -Amanda Haltmaier, Global Sales Development Director -Courtney Hayes, Senior Marketing Manager -Sloan Kendall, Head of Global Partnerships -Marcy Paterson, VP, Solution Consulting If you're interested in learning more, including the key roles Blink is hiring for, the full post is linked in the comments! And sign up for the newsletter to see who we bring you next week, will you?? #bostontech #startups #saas

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