Between Two COO's with Michael Koenig

Catherine Stewart is the former Chief Operating Officer at Shippo and Chief Business Officer at Automattic (WordPress),  joins us in part one of a special two-parter, to talk about the craft of scaling operations at hyper-growth tech companies. Topics include shifting strategic priorities at Automattic to also focus on revenue generation and e-commerce through the acquisition of WooCommerce, the shift from Facebook to Automattic, balancing the entrepreneurial mindset with the need for processes, not sugar-coating it, and why her time at Random House yielded some of the most valuable learnings of her career.Part two, coming next month, focuses on scaling the go-to-market and creating $B's in value.Shippo is a shipping software company backed by Bessemer and D1, where she led Marketing, Sales, Business Development, Customer Success, Customer Support, People Ops, and Strategic Planning. During her time at the company, Shippo's revenue grew 3x faster than the US eCommerce shipping market, and the company's valuation grew from $220M to over $1B in just 18 months.Prior to joining Shippo, Catherine was the Chief Business Officer at Automattic, the company behind WordPress.com, during the company’s growth from a valuation of $1B to $3B. While at the company, she led the acquisition and integration of WooCommerce. Previously at Facebook, she helped launch the Facebook Audience Network and led the three-year planning process, and at Random House, worked on the transition from physical to digital books. Catherine began her career as a strategy consultant at McKinsey. Stay up to date with Catherine at:LinkedIn: https://www.linkedin.com/in/catherine-stewart-800b841/Website: https://catherinetaylorstewart.comEpisode Webpage: https://www.betweentwocoos.com/catherine-stewart-part-one-peopleStay up to date with Michael at:  https://linkedin.com/in/mkoenig514

Doug Hanna, COO at Grafana Labs, dives into the rapid growth journey of the open-source observability platform that skyrocketed from a $5M to a $15M revenue stream. He shares insights on scaling commercial operations, the importance of customer experience, and the challenges of hiring in a competitive market. Doug emphasizes the significance of adapting go-to-market strategies and engaging with the open-source community. With humor and personal anecdotes, he reflects on startup lessons and Grafana's ambitious growth plans in the EMEA markets.

Doug Hanna, COO at Grafana Labs and former VP of Operations at Zendesk, discusses his journey in scaling companies during hyper-growth phases. He shares insights on rapidly growing Grafana Labs from 70 to 500 employees in just 18 months, emphasizing the importance of hiring for cultural fit and adaptability. Doug highlights the challenges of maintaining community and connection in a distributed workforce, and the balance between asynchronous and live communication for effective team dynamics, especially in the open-source environment.

Before Micah Rosenbloom was a venture capitalist, he was the co-founder and COO of Brontes Technologies, which he sold to 3M. Micah and his business partner Eric then went on to found the VC firm, Founder Collective, which has made investments in companies like Uber, ThreadUp, Hotels Tonight, Venmo, PillPack, and more. Micah joins us to discuss deciding who's CEO and COO, not shying away from tough conversations, hiring the right people, founding a VC firm and introducing ops to it, going through a transaction to a major corporation, the downside of making investments via Zoom, and how to identify investors that have true conviction in your company. Fred Wilson's post on working multiple jobs: https://avc.com/2021/10/working-multiple-jobs/Founder Collective: foundercollective.comMicah Rosenbloom on Twitter: https://twitter.com/micahjay1Micah Rosenbloom on LinkedIn: https://www.linkedin.com/in/micah-rosenbloom-a0350/Eric Paley: https://twitter.com/epaley/Raj De Datta: https://twitter.com/rdedattaScott Belsky: https://twitter.com/scottbelskyBill Tranchard: https://twitter.com/btrenchardChris Dixon: https://twitter.com/cdixonJames Tamplin: https://twitter.com/jamestamplinDave Frankel: https://twitter.com/dafrankelMichael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 Michael Koenig on Twitter: https://twitter.com/mkoenig

After doing $26B of M&A at Diageo, Marie Prokopets joined the startup world, and together with Hiten Shah, founded Nira.com a way to secure your company documents and access controls. As COO at Nira, Marie joins us to talk about pivoting from search to security, context switching, and what happens when vendors mess up access controls.Nira.com Marie Prokopets on Twitter: https://twitter.com/MarieProkopetsMarie Prokopets on LinkedIn: https://www.linkedin.com/in/marieprokopetsHiten Shah on Twitter: https://twitter.com/hnshahMichael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 Episode website: https://betweentwocoos.com/nira-coo-marie-prokopetsTranscript: https://betweentwocoos.com/nira-coo-marie-prokopets/#transcript 

Tucows Chief Product Officer, Justin Reilly, joins as our first non-COO, and shares on your customer's best last experience, how product design influences operations and where AI fits, Ting's amazing customer care, and how photos almost pushed a launch.Justin focuses on building the next generation of consumer products, particularly where AI meets customer experience. Prior to Tucows, Justin was Head of Product & CX Innovation at Verizon. He founded Focus Health, Grey Seven Labs, and Qstir. He was a Director of Strategy and Experience at Macquarium, lead the Strategy and Innovation team at Arke Systems. He currently advises a number of startups focused on the next generation of AI platforms and products.Justin Reilly on LinkedIn: http://www.linkedin.com/in/justinreillyJustin Reilly on Twitter: https://twitter.com/justinMreillyJustin Reilly on the web: https://justinmreilly.comTucows: https://tucowsTing Fiber: https://ting.com/internetEpisode Webpage - https://betweentwocoos.com/justin-relly-tucows-chief-product-officerEpisode Transcript - https://betweentwocoos.com/justin-relly-tucows-chief-product-officer#transcriptMichael Koenig - https://linkedin.com/in/mkoenig514

True Ventures Chief Operating Officer, Jim Stewart, on what it's like to take four companies public, what goes into the operations to run a venture capital firm, how to take calculated risks, and what to do when you realize that you've just violated US government export controls when you're doing an IPO roadshow (don't panic).True Ventures is a venture capital firm with an astonishing track record of investing in the best companies like Peleton, Fitbit, Ring, Duo Security, Automattic, and Sweetgreen, which just went public on the New York Stock Exchange.Jim initially joined True Ventures as CFO in 2012 and now leads all operations as the firm's COO. He brings substantial operational and financial experience to venture-backed tech and biotech companies. Jim has held numerous operating and CFO positions, leading four companies through their IPO processes. When he is not focused on operations, he's doing all sorts of high-octane activities like racing his Yamaha R6 motorcycle.Ben Horowitz's Book, The Hard Thing About Hard Things - https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205True Ventures - https://trueventures.comJim Stewart - https://www.linkedin.com/in/james-stewart-b1b10320/Episode Webpage - https://betweentwocoos.com/jim-stewart-true-ventures-coo Episode Transcript - https://betweentwocoos.com/jim-stewart-true-ventures-coo /#transcriptMichael Koenig - https://linkedin.com/in/mkoenig514

The podcast discusses Allie Fleder's journey from founding a luggage delivery platform to leading a fintech app. Topics include adapting as a startup COO, challenges of remote work, communication in early-stage startups, and motivating team members.

Rich Wallach, COO, and CFO of Deepak Chopra's Chopra Global, joins us to discuss:How a philosophy degree prepared him for everything and nothing at the same timeCredit Suisse's attempt to crush the humanity out of himCreating security, safety, and certainty for employeesOver-communicating without stressing people outHow processes can improve peopleGetting rid of the office and going fully remoteAnd lemurs. Yes, lemurs, the animals.Chopra Global: https://chopra.comChopra Global's Brand New Mobile App: https://chopra.com/appChopra Global's Upcoming Events: https://chopra.com/retreatsRich Wallach on LinkedIn: https://www.linkedin.com/in/wallachrEpisode website: https://www.betweentwocoos.com/deepak-chopra-global-coo-rich-wallachBetween Two COO's: https://www.linkedin.com/company/betweentwocoosMichael Koenig: https://linkedin.com/in/mkoenig514Running Remote: https://runningremote.comRunning Remote 30% Coupon Code: betweentwocoos

Between Two COO's: www.betweentwocoos.comMichael Koenig: https://linkedin.com/in/mkoenig514