Paul Upton’s Post

Should you leave your high-paid job to join a startup? (Considering this shift requires bravery) Staying in your comfort zone may limit your growth, while stepping out opens doors to personal and professional development. Okay now let's see your journey as a founding member → Onboarding & Learning: Align with the startup’s mission. → Facing Challenges: Build resilience. → Networking & Collaboration: Essential for success. → Leadership Roles: Drive innovation and manage teams. → Growth: Overcome setbacks and grow. Okay, now let's talk about how to evaluate a startup before joining? → Vision & Mission: Align with company goals. → Team: Assess compatibility. → Market: Check growth potential. → Product: Ensure market fit. → Financials: Evaluate stability. → Equity & Compensation: Understand the package. → Risk Tolerance: Know your comfort level. → Work-Life Balance: Consider the impact. → Opportunities: Look for growth. → Culture: Ensure alignment with values. P.S. Have you ever considered making this leap? Share your thoughts below. ♻️ Repost this for your network. Thank you!

Today is my last day at HUB. It has been an intense, rewarding, sometimes frustrating journey. I regret nothing. When I joined three years ago, there wasn't even HUB—just a bunch of people trying to figure out how to start. There were zero lines of code, an evolving idea of what the product(s) should look like, and lots of PowerPoint decks. Starting the build took some time, but in less than a year, we put together an enterprise-grade post-trading platform processing trades for some of the biggest asset managers in the world—quite a feat. That said, my biggest achievement was building a high-performing team of excellent individuals. It turns out it is easier than you think: hire the right people and spend your time protecting theirs so they can do their best job. It works every time! Finally, I also learnt something we all know implicitly: you can't "build" a culture. It will just emerge, and your best chance as a leader is to hire well and set good examples. As for what’s next, working at an early-stage startup meant my focus was always on the present. Now, I'm taking a break to ponder my future and my next career move. I’m excited about this next chapter and the opportunities it might bring.

SOS 🆘 It’s a beautiful new week, another opportunity to make a difference- be it small or big- A chance to impact! What advise would you give to someone who is new to your field/ role or someone about starting in your role? I’d go first🤭 🚻The idea of hitting the ground running is noble but allow yourself ease into your new role with grace. Don’t make major changes on the team you’re just joining in the first month(s). There’s more than meets the eye. Learn the internal process and operations. 📶📶 Existing employees are your friends not your enemies. Ask them strategic questions. How and why questions. ▶️▶️Have your 30, 60 and 90days plan, it will guide you to impact quickly on the team. ✅ We would love to hear from you.👏👏 You might be saving someone today! 👉What do you wish you could have learnt earlier in your career? Lay it bare I’m rooting for you 💪💪 Have a delightful week ahead? Remember your dreams are valid! Engage, share, and repost 🚀 #CustomerSuccess #LinkedInEngagement #SuccessManagerChronicles #letsconnect #customerexperience #customersupport #womeninleadership #saas #customerservice #career #careertips #jobseekers #womenleadership #fintech #startups

Here are 10 benefits of working in a startup over an MNC: 1. Greater Responsibility 🛠️ – You’ll have more hands-on roles and ownership of projects. 2. Faster Growth 🚀 – Startups often provide quicker career advancement opportunities. 3. Close-knit Team 🤝 – Smaller teams foster stronger relationships and collaboration. 4. Learning Opportunities 📚 – You gain exposure to multiple areas, not just your role. 5. Creative Freedom 🎨 – More flexibility to experiment with new ideas and methods. 6. Direct Impact 🎯 – Your work contributes directly to the company’s growth and success. 7. Startup Culture 🌱 – Dynamic and flexible work environments with a lot of energy. 8. Recognition 🌟 – Your efforts are noticed more quickly and appreciated. 9. Less Bureaucracy 🏃♂️ – Fewer layers of approval, leading to quicker decision-making. 10. Equity & Incentives 💰 – Potential for stock options or equity, leading to long-term financial gains.

7 years today - time flies! 🤯   I get a lot of interesting reactions when people find out I've been in sales at the same tech startup for 7 years. Not a surprise when average tenure of a sales leader is ~18 months... The majority of reactions are positive and curious, with some inevitable judgment — let them judge. More often than not, though, people ask me: “Why have you stayed?” When I reflect on why I’ve stayed, it boils down to these key reasons: Our customers and mission 🔥 Serving small business owners is incredibly fulfilling. These entrepreneurs are so deserving, and it’s gratifying to know we’re making a real impact on their lives through the product we provide. Hearing stories about owners doubling their revenue, taking their first vacation, or finally being able to attend their kids’ dance recitals or games because of Jobber’s support gives me chills. I’m inspired every day to put in the work to serve as many of these people as we can. And it helps that we have an excellent product to make it happen. The opportunity for growth 🌱 Jobber has provided me with incredible opportunities to grow—from being a first-time people leader to leading leaders and building entire teams and initiatives. I know I’ve been a risky choice for some of these roles at times, but I’ve always felt supported by great teams, peers, and leaders who’ve helped me succeed. The market opportunity 📈 The home services market is enormous, and the chance to build something truly big and special is incredibly exciting. We’ve made significant progress over the past seven years, imagining where we'll be in the next few is wild. My team 💪 I’m surrounded by smart, driven, mission-oriented individuals who are humble, supportive, and genuinely give-a-shit about what we’re building. You spend more time at work than anywhere else, I count myself lucky to spend it with people who make it fun and worthwhile. I’ve also had the privilege of watching so many talented colleagues grow their careers—from SDRs to AEs to first-time people leaders and beyond. Being part of their journey has been an honour. Spending seven years at the same company might be uncommon in the fast-paced startup world, and it might even earn me a few sideways glances. But I’m incredibly proud of what we’ve accomplished—the teams I’ve helped build, the results we’ve delivered for the business, and most importantly, the impact we’ve made for our customers along the way!

10 things that have helped me in my startup career:  1. Read  2. Exercise  3. Get good sleep  4. Follow smart people  5. Work on products you use  6. Keep a handwritten journal  7. Do the thing you're scared of  8. Keep connections with mentors  9. Develop a kind voice in your head 10. Work hard early if you're not more skilled I'll break them down and share how they helped me. 1. 𝗥𝗲𝗮𝗱 When stuck, I look for best practices. Often from books. In the year between my cubicle data entry job and landing at early Uber, I read 18 books. Stop feeling stuck - pull your next steps from the pages. 2. 𝗘𝘅𝗲𝗿𝗰𝗶𝘀𝗲 Every few months, I feel the world falling down. When I feel that way, I do an audit. I start by asking, "When did you exercise last?" Often, the answer is "weeks ago." So... I go for a run. And somehow, everything magically melts away. 3. 𝗚𝗲𝘁 𝗴𝗼𝗼𝗱 𝘀𝗹𝗲𝗲𝗽 This is similar to number 2. If I don't get good sleep: • I'm cranky • I'm pessimistic • I'm not as creative I spent good money on my bed. It has been worth every penny. As the saying goes, "Invest in your shoes and your sheets because if you're not in one, you're in the other." 4. 𝗙𝗼𝗹𝗹𝗼𝘄 𝘀𝗺𝗮𝗿𝘁 𝗽𝗲𝗼𝗽𝗹𝗲 I didn't find out about Uber from a press release. I saw one of the smartest people I knew leave a job at Goldman Sachs for a company I had never heard of. That company was Uber. A year later, I was working with him. 5. 𝗪𝗼𝗿𝗸 𝗼𝗻 𝗽𝗿𝗼𝗱𝘂𝗰𝘁𝘀 𝘆𝗼𝘂 𝘂𝘀𝗲 It's easier to land jobs at companies I'm excited about. I'll do whatever it takes to get in. Once inside, I do better work because I like it. 6. 𝗞𝗲𝗲𝗽 𝗮 𝗵𝗮𝗻𝗱𝘄𝗿𝗶𝘁𝘁𝗲𝗻 𝗷𝗼𝘂𝗿𝗻𝗮𝗹 My job search journal from 2013 became my roadmap in 2020 after a layoff. Journals can often provide the path forward. 7. 𝗗𝗼 𝘁𝗵𝗲 𝘁𝗵𝗶𝗻𝗴𝘀 𝘆𝗼𝘂'𝗿𝗲 𝘀𝗰𝗮𝗿𝗲𝗱 𝗼𝗳 Record and send a video. Create resources. Reach out to the person you admire. Growth comes from leaning into resistance. 8. 𝗞𝗲𝗲𝗽 𝗰𝗼𝗻𝗻𝗲𝗰𝘁𝗶𝗼𝗻𝘀 𝘄𝗶𝘁𝗵 𝗺𝗲𝗻𝘁𝗼𝗿𝘀 My manager from Uber helped me land my startup VP role. My COO at Avo has provided me with tremendous opportunities. Do good work and stay in touch with great people. 9. 𝗗𝗲𝘃𝗲𝗹𝗼𝗽 𝗮 𝗸𝗶𝗻𝗱 𝘃𝗼𝗶𝗰𝗲 𝗶𝗻 𝘆𝗼𝘂𝗿 𝗵𝗲𝗮𝗱 This has brought me the most joy and peace in the last two years. Listen to the way you speak to yourself. Would you speak that way to 5-year-old you? Become kinder and more encouraging. 10. 𝗪𝗼𝗿𝗸 𝗵𝗮𝗿𝗱 𝗲𝗮𝗿𝗹𝘆 𝗶𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗻𝗼𝘁 𝗺𝗼𝗿𝗲 𝘀𝗸𝗶𝗹𝗹𝗲𝗱 I never felt like the smartest. But I knew I could work hard. Early in your career, hard work can overcome a lot. It shows others you're worth investing in. Later in your career, you must learn to work smart (delegate, automate, eliminate). ------ If you like this, follow me, Kyle Thomas, for more. Like getting startup job search tips? Give this post a 👍 ♻ Share this to help startup job seekers find a new role.

"And then in my second year, I took on the project again." Great hires do the hard work that stymies others. One of the reasons I love being a search professional is that I get to hear about the exceptional work done in orgs that are already considered quite high-performing. Just today I spoke to a candidate who took on a technically complex project. This project was so complex, that in past years other people had led it once and burned out. But she wasn't going to be stopped by the challenge -- she wanted it to get a forecasting engine a highly impactful state where it could be useful year after year, rather than needing to be rebuilt from scratch. So the first year taught her all she needed to know about how hard it was. And when the second year came up, she volunteered to lead the initiative -- and this time take it from accretive gains to a transformative reworking. As founders aim to hires who can inflect the growth curves at a company, this is the kind of example that stands out as extrordinary. Amidst a team of ambitious high performers, what made someone go the extra mile? Knowing a project could lead to failure, what led someone to take it on? Not having to do something, why would someone excitedly volunteer for the tougher challenge? How a candidate speaks to all of this gets at their core DNA and motivations, and gives a peek at how they might tackle similar situations at their next startup. So in the end, it comes down one simple thing: It's not always about what someone did. It's about what someone did that made them exceptional, especially in the company of impressive peers.

Start-up or Big Corp? 🤔 --------------------- Choosing to work in a startup, despite the allure and stability of big corporation, was one of the most crucial decisions in my career path. The experience of working in a big corp was everything one might expect: structured, resource-rich, and full of learning opportunities. The training programs were top-notch, and I was surrounded by some of the brightest minds in the industry. However, I often felt like small cogs in a much larger machine. I wanted to see the direct impact of my work, to contribute to something that felt more tangible and integral to the company's success. That's when the opportunity at a startup presented itself. The idea of stepping into a role with such varied responsibilities was both exciting and daunting. The startup environment promised a steep learning curve, fast-paced decision-making, and the chance to make meaningful contributions from day one. The transition was not without its challenges. It was a leap into the unknown, but the potential for high rewards, both personally and professionally, outweighed the uncertainties. Looking back, choosing to work really pushed me out of my comfort zone, broadened my skill set, and provided a sense of purpose and fulfillment that I hadn't found before. 

The experience of being without a job after over a decade is both strange and invigorating. I'm not panicked or anxious; instead, I see it as an opportunity for change. Before this, I thrived in the fast-paced world of startups, constantly moving from one exciting challenge to the next. Each business brought its own unique hurdles, and I loved every minute of it. But as the years went by, that excitement gradually faded. In a way, I found myself craving this transition. I’d grown comfortable, balancing work with family life, especially as my kids moved into their teenage years. It was the right kind of balance, but part of me missed the thrill of the new and unknown. One thing that has stayed with me is the joy of working on UX in the Insurtech space. Whether it's building B2B or B2C workflows, I’ve found real satisfaction in shaping complex, unfamiliar processes that brokers, underwriters, carriers, and others use to simplify their work. Navigating and refining these intricate workflows has been a challenge I’ve loved taking on. So now, as I sit here contemplating the next chapter, here’s what I’ve realized: I love being part of teams that enjoy the journey of discovery. I’m drawn to solving unique problems that ultimately improve people’s quality of life. And I thrive on that ripple effect—when the improvements we make impact others in ways we didn’t even foresee. I also value the collaboration that comes from working across different departments, creating something greater together. I’m sharing my thoughts today because, as I explore what’s next, researching companies and opportunities beyond what I’ve done before, I’ve come to understand what truly excites me: the constant challenge of new, uncharted experiences and solving the problems that come with them.