Rachel Kaplowitz

It’s NY Tech week and my new favorite thing is teaching underrepresented founders how to talk back to investors. So many of them ask me for help fundraising, and I get it. I may not always think of myself as an expert, since I’m lucky enough to surround myself with people who are much more experienced at it than I am. But we did do it successfully once, raising more than $3M along the way with little more than a deck, a dream, and an incredible founding team. Of course, we’re all aware that this success puts us in the teeny tiny cohort of startups who raise without a traditional-looking founding team. So what’s the common theme in my advice to non-traditional founders at the early stage? Push back. It’s easy to get intimidated by investors. They’re smart, aggressive, and ask really hard questions. It can be hard to remember that YOU are the expert on your market. They are generalists. Even if they have strong opinions on your market, it’s OK to tell them when you think they’re wrong. In fact, if you have the conviction and confidence (plus evidence to back it up), disagreeing with your prospective investors can even be seen as an advantage. When a VC asks you a question at the pre-seed stage about your path to $100M in ARR, it’s OK to say “dude, we’re a pre-seed company. I know what our path is to get to a million, and we will have a lot to figure out after that.” Now, this only works if you have a track record that can support your confidence. Or if you don’t know the answer, but you DO know HOW you’re going to figure it out, talk about the path from experimentation to scalability. It’s better than making up a bunch of stuff that you’ll probably throw out eventually, and VCs will respect your focus and defense of your precious little time. Plus, they can usually tell if your confidence is lacking in your answer, anyway. This investor market is a tricky one, but never forget that they (investors) need you (founders) just as much as you need them. And hey, if you’re an up and coming female or underrepresented founder, and you need some help (or just a pep talk) I’d love to help. Happy Tech Week everyone!!

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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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Half of LinkedIn has already weighed in on Paul Graham's recent essay Founder Mode, which criticized the approach of running large companies with "efficient managers." The discussion was sparked by Brian Chesky, who, during an event at YC, lamented that hired management nearly destroyed his company. Everyone in attendance nodded in agreement. Let’s set aside the fact that guys in Patagonia vests may not be the best sample for assessing the success of "Founder Mode." The success of some of these individuals is hard to replicate, not just in other countries, but even in the U.S. under high-interest-rate conditions. Survivorship bias in action. The key question here is: are motivation and accountability for the company’s mission the critical factors for a startup's success? In my opinion, they come second, right after the ability to continuously learn and adapt to changes in the company. For example, the founders of Instagram stepped aside at the right time (maybe unwillingly), allowing efficient managers to build the second-largest social network in the world and a huge cash cow for Meta. An efficient manager, Imran Khan, came to Snapchat from Alibaba, helping the company make a great IPO and improving a lot as a CSO. Bill Gates handed over management to one of his early employees, Steve Ballmer, who in turn passed it to Satya Nadella, allowing Microsoft to become one of the world’s largest companies. Steve Jobs long resisted the necessity of releasing the iPhone and was ultimately convinced by multiple managers, who saved the company, which at the time was relying on a single product line. My conclusion from the stories above: one must constantly learn and evolve to align with the product's tempo. If you fall short due to a lack of skills, motivation, or health, it's better to let more flexible and competent people handle these challenges. You can't blame failure in people management on an inherent flaw in the hired management system.

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I call them the anti-buyers. Though IT and Finance aren’t usually the folks picking new products for their companies, they are often the ones with the power to shut a deal down. If Finance has concerns about cost or IT raises flags about interoperability, they can pull the plug on even the most promising contracts. It's in a revenue organization’s best interest to: Factor these critical stakeholders into the equation from day one so they get answers to questions that your primary contact may not know to ask. Make sure that representatives from these important groups are on the buying committee, and Marketing teams need to consider their needs just as early in the process. Ensure these two groups operate in lockstep as they communicate their products’ benefits to these often-overlooked contributors.

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I’m fortunate to spend time with a small group of people whom I consider to be the next generation of startup c-level executives. These folks have a lot in common. They’re often in VP level roles, have crazy high ceilings, and they’re perpetually looking to take their game to the next level. They’re running hard. Really hard. Oftentimes, they’re running just as hard at home. In many cases this career apex seems to coincide with having a young family. Sometimes, they run until they crash. I find this comes up a lot in our conversations. I’ve been there. I’ve seen good people leave good companies simply because they’re tired. Longevity is about maintenance. I'm into maintenance. Here are five maintenance strategies that have worked for me; 1/ Align time and priorities. In startups workload exceeds capacity so you need to decide when you work and what you work on. This is a life decision, not a business decision. 2/ Develop a maintenance process to increase longevity. What are you doing daily, weekly and monthly to ensure you’re operating in easy mode? 3/ Understand the power of identity. Exercise caution if what you do is who you are. Startups are volatile and high risk. Detach professional failures from failures of self. 4/ Play the infinite game. Understand that the game you're playing has no finish line. The goal is to keep playing and find joy in the pursuit. 5/ Build a personal board of directors. Startups may be for pirates and romantics, but that doesn’t mean you have to face the world alone. Building a network around you will help commiserate and think through difficult problems. More here, On Longevity: https://lnkd.in/duMCPtSV

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🎨 📺 Sharon Roth is a Product & Design leader who’s built her career in the lab, across different modalities, to bring more creative product experiences to life 📺 🎨 It's W3 / Q3 / 2024 and this week in our MGMT Boston up & coming operator series we’ve got Sharon who serves as the Senior Director of Product Management at Quantified.ai, the AI-driven flight simulator for sellers. The app feels as real as your next video call, scales across teams, programs, and companies, and ramps reps 42% faster. Sharon is leading Quantified AI’s Product & Design team after previous roles in Product leadership at Tamr & Honor Education. She’s excited to be back working in an Enterprise focused company, leading Design alongside Product, focused on strategic & execution based discipline. ❓Questions Are Your Roadmap ❓ It’s popular to encourage new hires to ask a lot of questions. But it’s always a good time to ask questions! When a member of your team comes to you and says “we really need to build X feature”, they’re coming to you for good reason. Dig into the why to understand how often the issue comes up, when it happens in a customer conversation, and why they’re asking for it in the first place. Is there an even better way to build a solution? Also, people are always excited about getting to a solution. By delaying the solution discussion to first get everyone to agree on the problem, you can coordinate a better response. Sharon has been in rooms where stakeholders can’t agree on the problem they’re trying to solve, which can sometimes be even more painful! By asking better questions and articulating the underlying issues thoroughly, they can work together as an organization to chart a better path forward. 3 Career Insights / Learnings 🙋‍♀️ Seek New Challenges - “Trying new things is how you learn and grow. At a startup, there are so many opportunities to try new things. As startups evolve, you need to embrace all that’s going to happen and make it a positive thing. Otherwise don’t go to a startup!” 🤝 Act with Integrity - “Do your best, show your work. But also treat others with respect and kindness while doing it. How you treat people and how you show up every day will impact your work environment. You’re responsible for the energy you bring to the room, so be authentic and try to inject some positivity. It will help you build the type of network you want to have too” 🗣 Invest in Communication Skills - “It helps you ask questions well, advocate for yourself, have your ideas be heard. It also helps others understand your impact. It takes continuous practice to do well.” If you’d like to learn more about Sharon’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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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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🌇 💡NY Tech Week Musings: 3 Days, 3 Thoughts:🗽🚀 Hey everyone, we're halfway through the adrenaline-fueled ride that is New York Tech Week, and boy, do I have 3 thoughts to share! 1) 🌍🤝 Connection Cravings Are Off the Charts With over 200 official events today alone (June 5, 2024), it's clear that people are hungry for networking. I mean, most events are so packed, you can barely squeeze in! It's amazing to see founders and investors from all over the world coming together. The global tech community is truly something special. 2) 🎉🗣️ The Great Networking Paradox Is it just me, or do some of these "networking" events make it nearly impossible to actually network? I feel like I'm shouting over the music half the time! 🎧😅 I love a good party, but maybe we could tone it down a notch and actually hear each other speak? 😆 3) 🌇🔍 NYC Tech Scene: Untapped Potential Alert Chatting with NYC folks, I keep hearing the same thing: we need a better way to stay connected beyond Tech Week.💡 There's so much potential here, and it's up to us to build the community we want to see. 🛠️🌍 So, fellow tech enthusiasts, let's not just network – let's build something awesome together! 🚀 If you're down to create a community that goes beyond a single week, hit me up. I'm all ears (and excited to see what we can create)! 😄✨ #NYTechWeek #newyork #techweek #networking #community I think the video here from one of the events yesterday is a great illustration of the overall spirit of the NYC Tech Week 👇

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A standard approach to new hire equity for public tech companies is a new hire grant ~2x the refresh grant, followed by annual refreshes, all with 4-year standard vest. The problem with this approach is the big drop off in vesting in Year 5 — in effect, you’re signaling to employees that’s the time to leave. How can we avoid this cliff? A simple way to accomplish this goal is with the combination of a front-loaded new hire grant and ratable refreshes. The key drivers to make this program work are: Front-loading the NH grant — this helps eliminate the cliff in year 5 Reducing the NH grant multiple — this also reduces the cliff, and lowers total spend Moving to 3-year vests — this pulls more vesting value forward Notice this actually saves the company money too. When we lower our new hire multiple from 2.0x to 1.5x, should we be worried it’s less attractive to the candidate? I think no, for a very specific reason: people rationally discount future value. Check out my full post below. 👇 And this isn't the only solution - how else can you adapt your stock comp design to minimize cliffs? #compensation #totalrewards

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Roon's most recent launch, Roon Fertility, is an exciting one. If you're navigating a fertility journey, or are even fertility curious, I encourage you to check it out! It's a labor of love that brings you trusted responses to any question – all through short-form videos and AI instant answers, powered by fertility experts. From the very basics (Should I freeze my eggs? What factors impact male fertility?) to the most specific (Can I do PGT-M to select embryos without the BRCA mutation?). Personally, it's been a dream to work with my childhood idol (and name twin), Olympian Tara Lipinski, to bring this to life. Check out this People article on why she's passionate about Roon: https://lnkd.in/e3BpxgdY & join Roon for free at roon.com

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From branding to remote work, discover how a $18B founder navigates growth, culture, and operations for sustained success 👇 Logan Bartlett (Managing Director at Redpoint) interviews Vlad Tenev (Co-Founder at Robinhood) to provide valuable insights on branding, culture, operations, and maintaining a long-term perspective in “Ep 105: Vlad Tenev (CEO, Robinhood): The Meme Stock Crisis, The Future of Crypto, and AI Opportunities in Finance”. Check out the key insights in the attached presentation 👇 ───── 👉 Follow me, Alexander Small, for tactics and strategies for building startups from industry-leading Founders, Operators and Investors

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🚨 The former CFO of Dropbox, Sujay Jaswa oversees the investment and operating activities as a founding partner at WndrCo, alongside media vet Jeffrey Katzenberg. He joins us for VC Wednesdays.🚨 🖋️  You recently closed a $460 million VC fund. Where are you looking to deploy that? Everything we do is around the idea of the future of work and helping people optimize how they get work done. That’s why we're investors in companies like Airtable, Figma, Databricks, Deel, 1Password and others. That won’t change, but now, you'll see us really focus on the applications of AI that will meaningfully disrupt how work gets done, like in finance, HR and customer support. 🖋️  Why should founders work with WndrCo? One thing that we do that's different is starting one to two companies a year in areas that we think have the potential to yield big returns. So, when we talk to entrepreneurs, our operating experience stays current, and that angle on venture is fairly unique. The second is that each partner at WndrCo has built something, so we have the empathy that comes from that experience. Third, we do only five to seven deals a year, versus bigger firms that do hundreds. Because we have a smaller portfolio, entrepreneurs can get a hold of literally every partner within a couple of hours, 365 days a year. 🖋️ Which startup pitch sticks out the most in your memory over others and why? My favorite is one that’s not a household name yet, even though the business is absolutely on fire. It’s Aura, an all-in-one product to protect you and your family online. The idea is that unlike the physical world, you have no idea what your kids are doing on their phones and devices. Aura gives parents the tools to navigate raising a kid in our mobile-first and digital-first world. When the founder, Hari Ravichandran, walked me through how he would take it to market, it was love at first sight. He's an extraordinary entrepreneur and the best go-to-market person I've ever met when it comes to consumer products. 🖋️ What’s one investment you regret passing on and why? At the end of the day, this whole business is built on being part of monster companies as early as possible. One of the best enterprise companies of the last decade is Databricks. The founder and CEO, Ali Ghodsi, is a very good friend of mine, and for whatever reason, it never occurred to me in the early years to twist his arm to try and let him take our money. We invested in Databricks later than I’d have liked to. 🖋️  What’s the biggest thing you’ve learned working with Jeffrey Katzenberg? The biggest thing I've learned is that you can't be him, and it’s impossible to keep up with him. He's relentless, and I have never met someone who works harder than him. If he says he's going to do something, no matter how hard, if it's within his capabilities, he'll do it. He's a doer, and he just gets stuff done. I admire that so tremendously. #VCWednesdays #vc #venturecapital #startups #TechonLinkedIn

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You have the power to create a million dollar community business. How? That’s exactly what Gina Bianchini, CEO of Mighty Networks, explores with me on the most recent episode of The Expertise Economy Podcast. In this tactical conversation, Gina introduces us to the 'People Magic' framework—a revolutionary approach to building thriving and self-sustaining communities. From identifying your ideal member to the 9 steps for creating communities so valuable you can charge for them and so well-designed they run themselves, this episode is packed with actionable insights that can transform your business and your members' lives. Whether you're a #creator, #entrepreneur, or aspiring #community leader, this episode is your roadmap to success in the digital age - don't miss this opportunity to learn from one of the leading voices in community building. Tune in and uncover the strategies that transform passion into profit: https://lnkd.in/dicjVMiB

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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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April was a big month for the Everything Marketplaces community! Here's a few highlights from our monthly roundup & recap post that I shared: -We're now 2,300+ marketplace founders & teams in the community -We had really incredible group chats with Casey Winters, Sara Mauskopf from Winnie, & Marco Zappacosta from Thumbtack -We had lots of other online events like our female founders meeting, fundraising meeting, & weekly office hours -We had meetups in New York City (at FJ Labs) & San Francisco (at Craft Ventures) -We had lots of founders share wins like launches, closing funding rounds, & also hitting major growth milestones + lots more Looking forward to another big month in May and also sharing some exciting news for the community soon!

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Excited to announce that Stigg has raised $17.5M in Series A funding! 🎉 Stigg is revolutionizing how software companies build and manage pricing models by introducing the first unified monetization platform for engineers. On a personal level, the story of Dor Sasson and Anton Zagrebelny is super interesting and inspiring, all the way from early ideation and co-founder search, to the exceptional product Stigg is today, and the exceptional team that makes this magic happen!

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It's impossible to find one mentor for everything. I believe in assembling a personal advisory board. Here's what mine looks like: - [friend in strategy at F500] for work and life advice - [former Lyft exec] for execution - [3x founder] for strategy and surviving the rollercoaster - [former investor] for market landscape - [exec coach] for exec coaching stuff - [many founder friends] for specific domains - [climbing coach] for climbing, training What does your advisory board look like?

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Working for a startup is fun but risky. So, here comes my green banner. I'm available from October. 🤩 I've tried a career change for the weekend (pictured), but I think I'd stick to what I know. 💪 After more than 5 years at Bitrise — a Y Combinator company —, 1.5 at Transcend and half a year with Rabbit, I’m looking for my next role in #productmarketing, #contentmarketing or as a(n early) startup #CMO. TL;DR: my portfolio is here: https://lnkd.in/dcRUYFd6 I could throw in some marketing lingo with all the #Reforge I've done over the past years, but first, let me try something different instead. :) Some of the highs or I unapologetically shine while - explaining complex tech concepts in a simple, understandable way, including whys and benefits - creating various types of content: blog posts, video scripts, messages, and emails to drive growth and pipelines - hosting or co-hosting webinars, podcasts or making videos - doing product demos, courses or enablement sessions - talking to customers: in person or online - talking to all the devs, including manning the booth at events - talking at all the devs, with me on a stage or on the screen - pulling strings together, working with multiple teams and stakeholders (aka GTM) - making order out of chaos - creating demandgen strategies and starting up marketing as such My dream job at the moment is - #remotework or in Budapest (close to 11th) - at a multicultural/international company with bright people and a sense of a mission - working as a full-time employee Developer tooling is a niche I’m familiar with and it fits like a glove, and I'm pretty much into cloud too, but I’m happy to be convinced to try something new. :) Please reach out if you know of any incredible companies that match my personality and talents, and could benefit from my enthusiasm, can-do attitude and inspired, deadline sensitive creativity! (You can also check out my portfolio linked above or my profile for some specifics and recommendations.) So, hit me up with recommendations. Thanks! #OpenToWork

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