Chris Caruso

How do I hire someone who's seen scale, yet is still scrappy? Aptible posed this question to us and we went to work: It quickly became clear that some of the most talented candidates weren't just working at high growth startups, but within larger companies known for aggressive scale and engineering excellence. But founders are often hesitant to hire someone with lots of big company background. They're fearful there's going to be a DNA or velocity mismatch. That's where it's important to dive deep and peel back the layers of the onioin. Our conversations with Nhien Tran pretty quickly revealed some extremely promising stories. As a critical PM owning the browser side of Datadog's Realtime User Monitoring product, she had learned to work within a smaller team that needed to prove it could punch above its weight to justify more resources. When the need for a React SDK emerged, Nhien led her engineering team to create one quickly, marshaling engineers that had never built one before to treat it like an internal startup. And most critically, she had seen a rapid scaling in her product areas, seeing customers provide real time feedback and enthusiasm about the value that she was delivering. And when you enter a smaller company -- that's often the biggest question founders worry about with a PM. Are they going to build the right things quickly, or are they going to spend lots of time building smart but unneeded things? Nhien answered that question head on at every step of the interview process. Hats off to an incredible partnership with the team at Aptible, including Caroline Lau and Frank Macreery for being great collaborators during this process. And amazing work to our search lead Nikki Bruno for her endless passion in filling this role! Nhien -- we're excited to see what you do!

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Founders from YC, A16z, TS backed startups I work with typically leverage one of these three strategies when hiring remotely Here's the breakdown: 👉 Direct Full-Time Hire: ↳Execution: Bring on board a full-time engineer with a direct contract. ↳Compensation: Pay through an Employer of Record (EOR) or directly via platforms like Payoneer or Wise. ↳Best for: Seamlessly integrating engineers into your core team who are poised for long-term growth with your startup. Ideal for roles that are central to your tech strategy. 👉 Full-Time via Employer of Record (EOR) ↳Execution: Employ a full-time engineer via an EOR, which takes care of all legal and administrative duties. ↳Compensation: The EOR manages payroll, taxes, and compliance concerns local to the engineer. ↳Best for: Startups aiming for quick scale without the hassle of navigating local labor laws and tax complexities. Perfect when expanding into new markets without establishing a local corporate presence. 👉 Staff Augmentation ↳Execution: Partner with a staffing agency that provides engineers on a contract basis. ↳Compensation: Pay the agency a rate that covers the engineer’s salary and a markup fee. ↳Best for: Startups needing to dynamically adjust their engineering teams to tackle project-specific demands or fill particular expertise gaps on a temporary basis. Ideal for short-duration projects requiring niche skills.

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How did a YC founder scale from $0 to $4M+ ARR in 6 months? What I learned surprised me: Getting to $200k ARR is possible through just hacking something together. But to break past the $1M ARR mark and keep scaling? To sign enterprise contracts with name brand companies? That's a different milestone. The fact that a technical founding did this and handled it all through founder-led sales is even more astounding. Surely, there must be some kind of secret sauce, some kind of unexplained context, I wondered. How did 2 technical founders who graduated college recently build something so robust, so performant and scalable, that they had enterprise companies lining up left and right? But no -- the founder let me know they did this through great engineering and sheer force of will. No proprietary edge. No silver spoon. No past domain experience. And in that moment, that simple answer made sense. We've also been speaking with amazing product engineers, many of them former founders, for whom things are just easy. Sometimes they cite great engineering mentorship as the key to their success. But more often than not, they simply "get it." And my team and I have over time honed our ability to naturally spot what makes a certain candidate special. It's a unique combination of high horsepower, high grit, incredibly sharp slope growth, and an ability to parachute into any problem and just figure things out. What seems like a quarter-long epic to some folks is a one-week project to others. New domains are never daunting. Never learned GPU inference optimization? No problem. I'll figure it out. This is the kind of talent that all startups need -- but understandably is truly rare to secure. This is the truly great, truly unique product engineer. And startups are rapidly learning how this kind of talent changes their own growth trajectory.

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Building Propexo has taught me so much about multifamily PM software integrations: 1. Integrations are hard 🤯 If you're struggling to build an integration, you're not alone. I've spoken to many startups that spend 6 months on just a single integration. That's time and money not spent on high-value features & other strategic product capabilities. 2. Integrations enable GTM 🤝 Property owners and managers are increasingly demanding integrations as a prerequisite for doing business. If your product doesn't seamlessly integrate with the PM software they're already using, you'll find it difficult to close sales. 3. Integrations are costly 💰 Be prepared to spend tens of thousands of dollars upfront to access each API before you can start building an integration. Once it is built, you can finally start selling and making money to recoup the costs. Engineering time, lost sales, and upfront spending are massive challenges that can make or break a startup. That's our "why" at Propexo. We provide simple, effective integrations that allow proptechs to grow fast. #proptech #propertymanagementsoftware #integrations #founders #multifamily

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I’ve screened thousandsssss of technical resumes. And here's an easy, 3-minute-fix resume tip to help FinTech and Web3 tech folks stand out. The tip: include a company or team blurb under your title in each experience section. Before I show you how, let’s answer why it’s important. You want recruiters and hiring managers to spend as much time as possible viewing your resume. You want to give them every reason imaginable to keep reading. The longer you hold their attention, the increased likelihood of snagging an interview. And you do it by including relevant, desired information. Now, two big things to keep in mind: 1. It's typical FinTech/Web3 companies look for industry experience 2. It's typical startups look for other startup experience ---- Enter the good stuff. Ask yourself whether your experience is with lesser known startups or well known organizations. It may be a mix of both. Let’s say you’re at Ramp—a recognized FinTech leader—you could include a quick snapshot of your team’s impact. Under your job title, it might read something like: “Member of Ramp's Applied AI team that builds AI tools, saving customers over $400 million to date.” On the other hand, if you’re at a smaller, up-and-coming Series A startup like Gynger (which is an awesome company btw), a quick snapshot of the company could look like: “Gynger is a Series A FinTech startup simplifying the purchasing process for businesses and helping them finance and manage tech expenses” Simple right? Assuming you’re applying to roles you’re qualified for, this quick update can help tilt the scale in your favor. And again, you can do it in the time it takes your Keurig to fill up your coffee mug this morning. (No, it’s not a silver bullet, but every advantage counts!) PS - if you put this into action, shoot me a note if it helps or not!

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I've talked to 50+ crypto projects over the last few weeks and they're all looking for help onboarding KOLs (Key Opinion Leaders) Many are hiring agencies, BD people, assistants - just to fail miserably Here's what they don't get: Before we get into how to onboard KOLs, just know: KOLs won't fix your problems If users can't understand your product, if your value prop is not strong enough... then go work on fundamentals and then work with KOLs KOLs work great when they amplify sth that's already great Now, back to onboarding KOLs 1) Outreach Most of the teams I've talked to use cold outreach, copy-pasting the same DM over and over again If that's you, you need to stop that NOW - nobody likes spam This is how you win and set yourself apart: - Try to get a warm intro if possible (this is where agencies can help) - Personalize your outreach! - Own your pitch! 💡No agency can do a better job than you at pitching your product! 2) Why your project is a great fit Make it obvious why their followers should care about a project like yours! Share metrics that show traction, Social proof (investors, PR articles, etc) Demo about how to use your product 💡Onboard them to your product as if they were users! 3) Remove friction from generating content Ok so now they buy that your project is legit, but now are thinking how painful could it be to generate content? (yes many of them are lazy) 💡Share some of your own content that has worked, content from other projects/KOLs can work too 4) Landing a good deal Lastly, negotiating a deal that makes sense for both sides is what will make or break this process Make sure incentives are aligned 💡Remember: No deal is always better than a bad deal! That's all - there's not much else to it tldr 1. Personalized outreach 2. Make it clear why your project is a fit 3. Remove friction from generating content 4. Land a good deal If you'd like me to go deeper into KOL deals, please reply to this post and I'll follow up with you

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I'm noticing some founders run one-sided interview proceses. For many candidates, this is a concerning red flag. It's not that candidates don't want to answer hard questions off the bat. The ones unwilling to go deep are the ones who often aren't suited for startups and how fast they move. And the good ones relish a robust and challenging interview process. Rather, it's important for candidates to leave with a sense of excitement about the role, mission, and vision. And if a founder spends all their time screening out the candidate, with no time to invite the candidate into the fold there's insufficient conviction on the candidate end. We see a broad array of interview processes, so here's what I like to look for: A strong first screen will filter out about a third to a half of good candidates. You'll need 45 minutes for it because 30 is insufficient to go deep. But -- all candidates, regardless of whether they're passing on or not, should leave the conversation excited about the company and role. You want the candidates to go "oh wow, it would be awesome to partner with this founder and work on this, even if I don't have the perfect background." Unfortunately we're seeing some cautious founders take a different approach. All one-sided questions. No trust building. And the candidate leaves with a poor impression of the founder and the role, even if the company seems like it's doing well. The candidates just don't want to take on the role. We hear this in our backchannel debriefs. And this is why at Candidate Labs we take a consultative and also completely transparent approach. We share the brututally honest feedback with founders. And - most critically - we bring solutions. Just this week I've personally written at least four interview guides, all tailored for individual personas, that are designed to facilitate a better interview process. Because at the end of the day, these hires will often work shoulder to shoulder with a founder. They know it, and the founders know it. And that's why chemistry and personal connection is so important to create early on in the process.

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Traditional software tech moats are eroding. This is a conversation thats pretty hot amongst founders and investors right now. It's happening for two reasons: 1. There has been an explosion of SaaS tooling over the last 10 years. You can buy vs. build almost every part of the stack right now.  2. AI makes it faster and easier to create the pieces you ~do~ have to build.  What does this mean for the future? Most top tier founders are embracing this reality. They are realizing that future moats are all around who your customers are and the value you are providing to them. I love how Adrian Alfieri is going all in on this concept. Verbatim isn't the first to help create content for teams, but they are the first to make their site all about their customers. We will see more of this in the future.

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Your biggest advantage as a startup is interview speed. But not every early stage startup gets it: It's easy to end up triaging hundreds of inbound as a founding team. "Look at all our interest from Work at a Startup" is something I hear from YC founders all the time. But action doesn't always mean progress. And when the bar for a hire is higher than ever, most inbound applicants just aren't going to be a fit. I've seen internal recruiters spend hours a day on inbound rather than prioritize the strongest candidates. And in companies with a strict adherence to process, this means strong candidates can get booked one week and even two weeks out. Today I had a client who saw this happening and quickly course corrected. Instead of more screens with their head of talent, they worked with me to get priority conversations directly in front the founder. This easily saved a week in the interview process -- and the candidates were EXCITED. Strong founding teams understand that speed is a big advantage. And if you're starting out late in the race, playing catch up is very, very hard.

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Not sure if anyone has noticed... I saw a bunch of LI posts from YC's LinkedIn page showcasing (marketing) their portfolios. Almost immediately you have actual engineers and builders (mostly outside of SF) commenting on the technical limitations of said highly funded and valued startups. It's not verbose lazy commentary but actually very insightful and detailed "why would I use {YC portfolio}? When I can use {a,b,c} for 1/10th the cost". And such comments actually generate the most likes which for me signals x-SF/builder consensus on their amusement on how these folks got funded.

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A great post from Santosh Sharan below. The most important part: 'WE STARTED SELLING BEFORE THE PRODUCT WAS DEVELOPED' AI and DeepTech startups - PLEASE listen to this. You can't just build, build, build. You have to SELL! #ai #innovation #sales

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Good news for SaaS hiring, jobs? Saastr (via Adam Schoenfeld) reports: "Even the (Forbes) Cloud 100 felt the 2022-2023 SaaS correction. Last year, 33% of the Cloud 100 had *reduced* headcount over the previous 6 months. Only 55% had a net increase. 13% were neutral. This year is different. 80% have increased headcount in the previous 6 months, only 11% reduced. 9% are neutral. Open roles have increased massively. Up 66% Y/Y from ~4,400 to ~7,300 for this group". ------- Much of this growth is concentrated among a relatively small group of high performers. And, a small number is expanding in APAC. However, we know APAC expansion typically follows sustained company growth in the US. So we may well start to see flow from this rally in the back end of the year. Anecdotally I'm hearing about headcount growth plans for Jan 2025.

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Check out these tech giants: - Snapchat - YouTube - Lyft What's their common thread besides being successful and innovative? They've all used CTO-as-a-Service (CTOaaS) at some point. For early-stage startups, it can be a significant boost, helping them stay on track and build meaningful products. So, how can #CTOaaS drive your startup? And does it really shake things up? In some cases, yes. Here's why: You get access to experienced professionals who've tackled similar challenges without the hassle of a long-term commitment or searching for the right fit. It means you get immediate help for pressing needs without giving up equity or paying upfront bonuses - you pay for the value you receive. It also gives you time to develop your strategy and find a permanent CTO while keeping your business moving forward with the guidance of a fractional CTO. But, before hiring a freelance CTO, consider the following: ☑️Budget Constraints: Startups with tight budgets might not afford an executive-level service like this. ☑️Need for a Part-Time CTO: A part-time CTO isn't always necessary. CTOaaS is particularly useful if you're a non-technical founder but might not be needed if you have tech expertise. ☑️Existing Team Capabilities: If your current team can handle the CTO's responsibilities, you might not need extra help. ☑️Strategy Expectations: CTOaaS offers short-term guidance and support, not a long-term strategy. If you can manage without additional help, bringing in a contractor might not be urgent. Personally, I suggest you consider CTO consulting services if: 📍You have a tech idea but need more skills to develop it. 📍You've outsourced development and need expert review and guidance. 📍You're exploring tech for your products or preparing plans for committees or investors. 📍Your systems are outdated and need a refresh. 📍You want to reduce costs and improve staff flexibility without a full-time CTO. In short, CTOaaS is a smart way to get expert help with limited time and money. It can transform your business and drive significant improvements. Give it a thought.

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We've helped hundreds of tech startups build their GTM teams  and noticed a common mistake among first-time founders: ↳ They treat GTM like a short-term project  with a binary outcome: make it big or bust. We commonly hear something like: "We will 𝐫𝐞𝐯𝐨𝐥𝐮𝐭𝐢𝐨𝐧𝐢𝐳𝐞 𝐭𝐡𝐞 𝐰𝐚𝐲 𝐩𝐞𝐨𝐩𝐥𝐞 𝐝𝐨 𝐗𝐘𝐙" or "𝐛𝐮𝐢𝐥𝐝 𝐚𝐧 𝐚𝐥𝐥-𝐢𝐧-𝐨𝐧𝐞 𝐩𝐥𝐚𝐭𝐟𝐨𝐫𝐦 𝐭𝐨 𝐝𝐨 𝐘" (sounds familiar, right?) Their goal for the GTM team is vague: find people with good profiles (work at big companies, Ivy League graduates, Forbes 30 under 30, etc.), mostly to leverage their network to make some deals and beautify their deck to raise funds. In contrast, the most successful startups we've worked with approach this differently. ↳ They let their GTM teams be shaped by where they are on their "market-fit" journey GTM and product evolve in lockstep with each other. They consistently refine their strategies and team structure to meet changing business needs. Their product will go through three stages: 𝐏𝐫𝐨𝐛𝐥𝐞𝐦-𝐦𝐚𝐫𝐤𝐞𝐭 𝐟𝐢𝐭: Find a significant and worthwhile problem to solve. 𝐏𝐫𝐨𝐝𝐮𝐜𝐭-𝐦𝐚𝐫𝐤𝐞𝐭 𝐟𝐢𝐭: Develop a solution for this high-demand issue. 𝐏𝐥𝐚𝐭𝐟𝐨𝐫𝐦-𝐦𝐚𝐫𝐤𝐞𝐭 𝐟𝐢𝐭: Build a collection of multiple products that fit in the market. Each stage has different objectives, so the approach to building the GTM team should vary accordingly. In the first stage, most founders will do it themselves. Startup ideas often arise from everyday experiences —you see a problem, and you have an idea to solve it. You need to test if the problem is big enough.  Go to meetups, ask around, DM people like crazy. You can hire a sales rep to help with that.  BUT Their role isn't to generate revenue but to gather leads  that you can use to refine your ICP and improve your product. As you move past the ideation stage, your GTM focus will gradually shift towards Sales and Marketing and, eventually, Customer Success. ✅ I included the MOVE Framework from GTM Partners below. They do a great job showing how product evolution changes GTM approach. During the last 2 stages, you should hire people with domain expertise, especially if you sell complex technologies. Many founders make the mistake of hiring based on titles alone. Then, they find out their new hires totally get lost because they don't understand the technology. (even though they have solid sales backgrounds). You can't sell what you can't teach. So hire GTM talent that understand your product and speak your customers' language. P.S. Need help hiring a GTM expert team for Data, AI/ML, Compute, and Cloud Infra? DM me. We have helped successful early-stage startups (backed by Zoom, Norwest, and Two Sigma Ventures) find A+ hires. #GTMstrategy #GTMteam #recruitment #sales #strategy

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Measuring what matters 📏 There are four data points I've been helping a seed stage startup monitor and improve, alongside helping them build their engineering team. 1️⃣ Application to first interview ratio ➝ Why it matters: Highlights the effectiveness of job postings and hiring partners. 2️⃣ Time to hire (TTH) ➝ Why it matters: A quicker TTH helps secure top candidates, while a longer TTH can negatively impact candidate experience. 3️⃣ Lost talent at each stage ➝ Why it matters: Identifies potential process issues and areas for improvement. 4️⃣ Offer acceptance ➝ Why it matters: Indicates the strength of your company culture, mission, package, and talent qualification process. Getting clear on the data points that are most important to your business, why they are important, and how you are going to track them is essential. Make sure your partners understand your data points, and help you in the process of achieving your targets. If you're experiencing challenges in your hiring process. Book in a free discovery call using the appointment button on this post or on my page. #hiring #recruitment #hiringtips #datadrivenhiring #startup

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5 tools I use to grow climate founders’ LinkedIn: - AuthoredUp - great for formatting, storing ideas & content calendar - Fathom Builder - to create UTM tags when promoting their EECs - Notion - where all of my drafts, strategies, client portal sit - Otter.ai - transcribes our calls that I pull content from - Shield - the best LI analytics tool on the market These have never let me down. Tools that I tried but found to be overrated: - Taplio - nice auto-plug feature, the rest is overrated & overpriced - Folk - their sales rep is rude as hell and my Notion does everything Folk can “What do you use for scheduling?” Native LinkedIn is perfect. What’s your tool stack? — PS. This post is supported by AuthoredUp. PPS. But here’s the thing: I don’t use tools because I promote them. I promote tools because I use and love using them.

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