Olivia Joslin

📈 Curious about the startup scene in Massachusetts? Explore our detailed funding list featuring startup names, HQ locations, and investor info. Perfect for investors and entrepreneurs alike! Check it out: https://lnkd.in/dAp3xj-Q #startup #startups #venturecapital #funding #vc #managementconsulting

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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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🏛 PredictAP, Inc. is an AI-powered invoice capture platform to codify tribal knowledge and modernize software tooling in a traditionally “offline” real estate industry 🏛 It's W5 / Q4 / 2024 & this week in our MGMT Boston startup series we’ve got PredictAP, a team building the product they wished they had reconciling invoices, tax IDs, and payment flows to help real estate managers better allocate resources and capture efficiencies. Founder & CEO David Stifter worked for Colony Capital for almost 20 years and is an accountant by background (having studied locally at BU). He became an in house real estate technology leader and led a major ERP integration to Yardi, the industry standard real estate accounting software. His career was advancing. The migration went smoothly. Then Chrissa, who was a key player in Colony Capital’s AP process, retired (with her institutional knowledge). Colony ($43B in assets) moved a lot of money around and had an internal system that helped them reconcile payments, approvals, and invoicing through a complex ownership structure. Accounting rules vary depending on whether a property in their portfolio was a multi-family asset or an industrial asset. AP isn’t glamorous, but you can imagine the complexity as it relates to cash flows, invoicing, tracking, etc. So when Chrissa retired, poof! A lot of context went missing. David & his team built an internal “invoice coding system” tool and, a couple years later, David bought out the rights to the internal tool with his partner Russell Franks to build a proper technical infrastructure and see if this tool could help real estate managers more broadly. A year later the product was ready, and PredictAP hit the market running in 2021 to solve a very specific pain point: properly coding multi-line real estate invoices. So real estate teams can spend more time in the facility and less time manually updating spreadsheets and reconciling data. Today they have 80+ customers and can show clear 4-5x ROI on the time savings, let alone the resiliency they are building. The platform processes nearly 3M invoices annually, demonstrating its scalability. In November of 2023 they closed their $8M Series A and are on track to grow from six figures to mid seven figures of ARR in 2024. They expect to close the year at over 100% revenue growth and have seen existing customer revenue growth grow by 25%. With a team of ~20 employees, PredictAP is positioned at the intersection of real estate, accounting, and AI technology as a crucial player in the real estate accounting technology stack. Operators to Know (Locally): -Greg Achenbach, VP of Product -Kristina D., Software Engineer -Ethan Neidhart, Software Engineer -Ali Noel, Director of GTM Enablement -Tony Scalese, VP of Customer Success -Emma D Whitman, MPH, Product Manager If you're interested in learning more, the full post is linked in the comments And sign up for the newsletter to see who we bring you in the weeks ahead!

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Three lessons from building and launching a P2P payments app without doing the proper customer validation first (despite knowing better): 1) Building something you need is a great starting point - but not enough to validate an idea. As someone drawn to building solutions, I’m an early tech adopter. This led me to overestimate consumers’ willingness to onboard, especially with a P2P payments app that requires KYC/KYB compliance and relies on a network effect to be useful. 2) Manual solutions are often best to start with It’s good business to be in business - transitioning from ideating to operating as early as possible is the BEST way to learn effectively. While the move fast and break things mindset has attracted well-deserved skepticism, getting stuck in a multi-year build trap distracted me from critical real-world validation. 3) Consumer appetite shifts quickly In my case, the proliferation of free and instant P2P payment options like Zelle added additional pricing pressure that I couldn’t compete with. This disincentivized the consumer event/payment collection market, turning my bottom-up go-to-market strategy upside down. Pitch (https://www.pitch.fun) is currently on the back burner as I’ve begun building custom solutions in various industries to sharpen my skills, solve specific problems, gain a hands-on understanding of operations, pain points, and workflows, and build a network of experts to lean on as I keep my eyes peeled for high-impact opportunities.

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🚀 Venture debt covenants might sound like a small part of the deal, but they carry huge implications for your startup’s future. 📈 You need to be strategic in your negotiations to avoid any pitfalls down the road. It’s all about setting yourself up for success, not stress. Dive into more details in the original Kruze Consulting post. The link is in the 1st comment. 👇

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Bootstrapped Founders I work with are figuring out how to drive profitability. VC-backed Founders I work with? They're trying to figure out how to skip a round. If you're a SaaS Founder working to build a differentiated GTM Machine so you can control your own destiny, then grab a complimentary copy of my 5-Point SaaS Growth Strategy Guide. Follow the link in the comments below 👇

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Congrats to the Revive team for the latest fundraise led by Equal Ventures, as well as the new brand! I’ve had the honor of working with Allison Lee (Founder/CEO) and team for almost six years as their first institutional investor. My gosh, it’s been an incredible–and at times harrowing–journey… ‘Revive’ is such an appropriate name for this company, on multiple fronts. First, it describes the core business well, where this platform helps large retail apparel brands to upcycle garments and deadstock into new products, thereby substantially reducing apparel waste. But it also accurately describes Allison Lee herself. Allison is one of the most resilient humans I’ve ever met, and she’s gone through hell and back to create this outstanding company. When we were first introduced to Allison in 2018 (thanks Bebe Kim for that intro!), Allison was a solo founder experimenting with mall kiosks that provided on-demand hemming services for retail apparel consumers. Over the years, Hemster (the name of the co back then) scaled up to become a substantial business, with her own warehouses and staff to handle hemming for top apparel brands throughout the US. But then the pandemic happened. Brand clients budgets collapsed, along with her business model, and Allison had to reduce her team down to just one person. Herself. This was a dark time. I remember reaching out and attempting to check in with her during a six-month period where she was at her loneliest as a founder. She pretty much locked herself in her apartment, mulling new directions for her company by herself. But she figured it out. In 2021, she saw that the consumer retail market was shifting as Gen Z was strengthening their purchasing power. This new generation of shoppers were more climate and sustainability conscious, and wanted to hold big brands’ feet to the fire for products that conformed to their values. Allison saw an opportunity to retool Hemster into a top platform to help facilitate upcycled products for apparel companies. And it worked! Allison breathed new life into her company and business has been growing quickly ever since. Her business’ thesis is even stronger and bigger than the one she initially launched with. Beyond her being a skilled founder and operator, Allison is also a fantastic human being. She is relentless and un-killable as a founder. And also so warm, kind, and present as a friend. I’m grateful to call her a friend today, as well as a role model. Allison’s journey is still in the early days with Revive, and no doubt she is going to build something that has a huge impact on this world. Hustle Fund is nothing but grateful that she said YES to us, and allowed us to be part of this amazing and inspiring journey. Congrats again, Allison and team!

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This is an interesting article from SaaStr sharing data from ICONIQ Capital about revenue per employee. “These are useful yardsticks for folks scaling: At less than $25m ARR, actually SaaS start-ups aren’t any more efficient than in 2017-2019, at $130,000 per employee / FTE. Although that’s still more efficient than the Boom Times. At $25m-$100m ARR, SaaS scale-ups are about 25% more efficient than they used to be, at $172,000 in revenue per employee / FTE. Time to get real at $25m ARR, apparently 😉 And at $100m+ ARR, they are 20% more efficient then they used to be, at $249,000 in revenue per employee. On the path to the $300k+ we see in public SaaS leaders.” At Worksmith in October, our annualized revenue per employee was $238K. https://lnkd.in/gqkkpjEW

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In case you missed it last week, one of my favorite SaaS benchmark reports was released. Thanks to High Alpha and OpenView for the work and having us as a partner! This thing is stuffed full of insights on everything from growth rates, net revenue retention, ARR per FTE, and more. You can't build a great SaaS business without it! https://lnkd.in/ghKT_tBY

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🚨 hot take: I think the current early-stage VC environment overvalues growth hacking, sales, and marketing and meaningfully undervalues great products and engineering. The reality is that having great GTM and growth is incredibly important, but the best companies have the best products....and usually these products take a long time to build and are very hard to reproduce (even with the help of AI). THOSE are the companies I would bet on.

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The king of pivoting Slack founder Stewart Butterfield is certainly an extraordinary founder with an amazing story. While everyone knows Slack, I bet very few know that Slack started out as an online community game (at least I didn't). And when that didn't work, he went all in and took what worked best (the community chat) and built Slack out of it, which was acquired by Salesforce in 2021 for the astronomical sum of $27.7 billion! What's even more remarkable is that this isn't the first time Stewart has turned failure into success. His first startup success Flickr (the photo app) was also born out of a game. Here are a few more remarkable statements from Stewart: ➡️ „… the moment you find the thing that your users cannot stop doing, you need to slash and burn the rest of your business“ ➡️ „… as a founder, you never want to say “We’re working on X, and we’re also working on Y because my team likes both ideas.” That may be the expedient solution. But I can tell you how that story ends: like Thelma and Louise, holding hands and driving over a cliff together.“ ➡️ „… as CEO, you always have to bring the core team along during a pivot. You have to make them feel like it was a joint decision“ ➡️ „…If there was one piece of advice I wish I could phone back and give to myself, was just concentrate on that storytelling part, on the convincing people. Because if you can’t do that, it doesn’t matter how good the product is, it doesn’t matter how good the idea was for the market, or what happens in the external factors, if you don’t have the people believing.“ My 2 key takeaways: 👉 you need to win the people’s hearts 👉 go all in and double down on what works 🎧 Here is the link to the podcast (absolutely worth listening!): https://lnkd.in/eNAxab5t ____________________________ Sharing my experience as an entrepreneur and angel investor. Investing in early stage B2B SaaS startups. Happy to connect 👋

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Product market fit means different things across the VC landscape. If you ask a group of 100 VCs what PMF is you'd probably get 98 different answers. I appreciate Jason Cohen's take on PMF and his transparency on the topic. The roadmap is a 17 year long journey of figuring it out. Rather taking WP Engine from zero to unicorn status. The PMF journey demands prioritizing sales and marketing over product, since you will advance the product anyways. "Ask yourself: What can you do today, that will (a) get more people from the target market to come to the website or (b) convert more of those people to try the product or (c) convert more of those to buy the product." Another great point is passion. Do what you love, and the money will follow. — Motivational advisors "That is false, as evidenced by most artists, philosophy majors, and the 80% of startups that fail despite founders’ genuine love and obsession." Vincent van Gogh was an extremely passionate artist and throughout his life only managed to sell one painting. To his brother. The last 3 projects I was super passionate about found themselves in a graveyard — a text file in my Documents folder of all failed ideas. As Jason points out "You are scared that targeting only the ICP limits your potential market, but this is not what happens." Might be the primary reason as to why that digital graveyard in my Documents folder exists. PMF has no single definition but this could be a potential summary.. "Marketing is where you discover the promise the customer wants you to make, and retention is where you discover whether you’re fulfilling that promise." https://lnkd.in/es9TUNxW

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RevOps leaders, this is the playbook you’ve been waiting for. In a world flooded with content that often lacks substance, the RevOps Docs for Startups by LeanScale are a breath of fresh air. This guide isn’t just another rundown of the basics—it’s an in-depth, yet easily approachable, guide to the rapidly evolving RevOps landscape, crafted from real insights gathered across 50+ hyper-growth companies. Huge shoutout to my longtime buddy Joe Zaghloul and the team at LeanScale for putting in the thought and care to make something truly impactful. The format alone—structured like API docs, complete with a changelog—makes it incredibly usable and memorable. #RevOps leaders and #GTM teams will find it packed with playbooks that feel almost built-in to the process. If you’re scaling a B2B SaaS, you’ll want to bookmark this one. It’s hands-on, actionable, and unlike anything else out there. https://lnkd.in/ekrUJAW5

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WE DID IT! After 2 years of pushing through the biggest downturn in VC in decades, Matthew Stotts 🌐 and I made it to the finish line with Fund I! We couldn't have done this without One Small Planet (Will Peterffy and Jack Wielebinski 🙏), Regen Network and Regen Foundation (Austin Wade Smith Gregory Landua and Will Szal), and a dozen other family offices and angels who believed that we can build a nature-positive economy utilizing our eye for software and our history as founders from day 1 A shout out goes to all of our founders (only four announced today, but watch this space - there are multitudes!) who trusted us enough to give us a spot on their cap table for this 10-15 year journey. This is the best job in the world, and it's because we get to work with people like you who have weird ideas in the best possible way. Using Bitcoin as anchor base load to decarbonize residential housing in America's most expensive energy market? Make every complex supply chain legible to machines so we can find and eliminate deforestation in commodity supply chains? Build deeply liquid environmental asset markets to price ecosystem services, on a blockchain, that no one needs to know is a blockchain? I'm so excited to get to work on this stuff for the next 10-15 years minimum, and to see what we can accelerate with our tiny fund in the next 5-6 years as we approach 2030 Onward! https://lnkd.in/gy3B-DFe

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Next week, I’m hosting 15ish B2B seed stage founders to talk about what’s working and not working in GTM. Some of the things I’m hearing from other founders who are at that sub-20 customer stage have to do with growing beyond their network. Everyone seems to be able to find a couple customers or early design partners but how do you move beyond with limited resources? One of the founders I spoke to who is in AI, is leveraging the brand of AI to get conversations through cold outreach. A broad message of “We do AI for X generating Y results" where X is your niche audience is getting conversations started. These types of insights and the detail that goes with them are the things we’ll be discussing next week. Join us. https://lu.ma/x3k6v4dn

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I love this piece by 📈Aurangzeb Agha (my co-founder at Metrical, Inc.), which offers a simple guide to unlocking 40x ROI in one month using AI and machine learning. I especially love the 3 key takeaways that make up the 'Metrical Difference': 📖 Anticipate customer behavior 📈 Avoid reactive offers 🗺 Offer tailored shopping experiences Take a read here:

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Inspired by what we’re building at Build Momentum. We realized tech recruiting is broken—non-technical recruiters struggle to find and attract the best talent. That’s why we’ve flipped the script and developed a community-based recruiting approach: a trusted network of elite engineers, embedded within Latam’s top tech communities. The best engineers know the best engineers, and we tap into these deep, authentic connections to deliver top talent faster and with better fit. Want to see how we’re doing it differently? Check out our post

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Perfecting your product and GTM strategy are surely important. But Box CEO and co-founder Aaron Levie argues there's one factor that outweighs all others in startup success: recognizing and capitalizing on tech and macro tailwinds. Fighting against them? You're setting yourself up for failure. Our full conversation here: https://lnkd.in/gEAPFR-A

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🚀 Big news: ServiceTitan, a SaaS leader in field service management, has officially filed its S-1 to go public! With $685M in LTM revenue and 24% YoY growth, it’s clear the company has carved out a significant niche in the market. However, their -$183M net loss and growth rate bring challenges. By SaaS standards, ServiceTitan falls short of the Rule of 40—a key metric combining revenue growth and profit margin to evaluate efficiency and scalability. Their score is -2.7, well below the ideal 40%. Excited to see how the market responds—your thoughts? Let's discuss! #IPO #SaaS #Growth #Startups #Tech

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