#010: In this episode of DevEx Unpacked, Alan Carson sits down with Des Anderson, co-founder and CTO of LearnUpon, to discuss the journey from start-up idea to global SaaS leader.

Des shares candid insights on co-founding a company during uncertain times, simplifying the LMS market, scaling engineering teams, and keeping innovation alive with AI and horizon-two projects.

From navigating cloud choices to balancing tech debt, security, and customer trust, this episode is packed with lessons for SaaS founders, engineers, and product leaders building the next generation of software platforms.

• (00:00) - From Ireland to Serbia: Des Anderson’s Journey to Founding LearnUpon
• (02:30) - How Two Co-Workers Became Co-Founders and Built a SaaS Vision
• (05:00) - The Big Leap: Leaving Jobs and Taking the Startup Risk
• (06:30) - Spotting the Gap: Simplifying Learning Management Systems
• (10:00) - Going All-In on the Cloud: Building with Ruby on Rails and AWS
• (14:40) - Scaling a Global Business: Lessons from Japan and EY Entrepreneur of the Year
• (18:30) - Growing Pains: Engineering Challenges and Prioritising Tech Debt
• (24:00) - Product, Process, and People: Keeping Teams Nimble at Scale
• (30:00) - Building Future Innovation: Experimentation, Horizon Two Work, and AI Agents
• (34:30) - AI in Learning Platforms: Opportunities, Risks, and Red Tape
• (43:30) - Security and Trust: Building Enterprise-Grade SaaS from Day One
• (48:07) - Favourite Part of the Job: Culture, People, and Leading a Global Team

#009: In this episode of DevEx Unpacked, Cloudsmith’s Chief Strategy Officer Alan Carson chats with Kerry Boden, HR Manager and the force behind scaling Cloudsmith during its explosive growth.

Kerry shares her journey from linguistics to HR leadership, her experience joining a 35-person startup, and how she helped grow the company to nearly 90 employees across four continents.

Learn how Cloudsmith balances rapid hiring with culture fit, how remote onboarding can actually outperform in-office programs, and the secret sauce behind keeping employees connected, even when they’re thousands of miles apart.

From the magic of offsites and Slack culture to the emotional impact of "Cheers for Peers" and the dangers of remote burnout, Kerry gives an honest, practical look into how to build, and maintain, a thriving culture in a high-growth, remote-first environment.

Whether you're an HR professional, a startup founder, or just someone fascinated by how culture scales, this episode offers valuable insights on setting high hiring standards, prioritising wellbeing, and using tools and rituals to build lasting employee connection in the modern world of work.

• (00:00) - From Language Degrees to HR Leadership: Kerry’s Unlikely Path
• (03:51) - Joining Cloudsmith: Building HR from the Ground Up
• (07:19) - Scaling Fast: From 35 to 88 Employees in 12 Months
• (11:04) - Creating Culture in a Remote-First Company
• (14:22) - The Power of Offsites: Recharging the Collaboration Battery
• (18:09) - Internal Communication That Builds Customer Success
• (20:46) - Building Culture Across Borders and Time Zones
• (22:39) - Weekly Rituals That Keep the Company Connected
• (26:00) - Cheers for Peers: Recognition That Drives Culture
• (28:08) - Scaling HR: Tools, Teamwork, and Hiring at Speed
• (36:10) - Fighting Burnout in a Remote-First Startup
• (41:20) - Hiring High Standards: Why Great People Make a Great Company
• (44:28) - Final Advice for Remote HR Leaders

#008: In this episode of DevEx Unpacked, host Alan Carson sits down with Dave McConville, a customer success powerhouse at Cloudsmith, to explore what it truly takes to build lasting customer relationships in a complex, fast-growing tech company.

Dave shares his candid journey from aspiring software engineer to technical writer, scrum master, and ultimately, the go-to guy for making customers successful.

With humour and deep insight, Dave unpacks the realities of artifact management, navigating curveballs post-sale, and the critical role of empathy, transparency, and trust in building partner-like relationships with customers.

He discusses the early days of Cloudsmith, what it's like to move from Belfast to New Jersey as part of a remote-first company, and how he balances technical knowledge with human connection.

Tune in for practical wisdom, real stories, and a behind-the-scenes look at what makes Cloudsmith’s approach to customer engagement truly special.

• (00:00) - Finding the Path to Cloudsmith: From Code to Customers
• (03:15) - Life as a Technical Writer: Writing for Readers Who Don’t Read
• (06:05) - Early Days at Cloudsmith: Chaos, Buckets, and Building
• (09:54) - The Handoff: How Sales Transitions into Customer Success
• (13:59) - Artifact Management Is Never Boring
• (15:26) - Building Trust: How to Win Customers Without Knowing Everything
• (20:23) - Dealing With Curveballs and Growing With Customers
• (25:11) - What Success Really Looks Like in Customer Success
• (26:35) - Moving to the U.S, Time Zones, Slack, and Coffee Overload
• (32:33) - Defining Customer Success From the Ground Up
• (38:09) - The Intercom War Room: Support, Sausage Making, and Real-Time Fixes
• (44:17) - Why Customers Love Dave: Relationships Over Transactions