
37 segments available
Allison Pickens is the former COO of Gainsight and one of Fortune’s Most Powerful Women. Throughout her time there, she scaled the SaaS company from $1M ARR to pre- IPO, along the way, creating the category of customer success software, and paving the way for Gainsight’s $1.1B sale. Today, she advises and invests in companies on these topics and others. Allison is an incredible builder of teams. She’s written extensively on the topic and co-authored a book The Customer Success Economy. In addition to talking about the evolution of customer success, Allison and I will talk about the COO role. COOs have become more common in management teams as ways for founders & CEOs to build the management team to scale a business. In conversations with management teams, the concept of a COO remains murky.
In this opening segment, the hosts introduce the session, highlighting the excitement around having Allison Pickens and Tomasz Tunguz join the discussion. They outline the format of the event, including Q&A opportunities and the interactive nature of the session, setting the stage for an engaging conversation about customer success and the COO role.
"[Music] all right we are good to go good morning all from san francisco i thought i would switch up office hours this week and come from another room of the apartment here in nob hill we are excited w..."
Allison Pickens discusses the increasing prevalence of Chief Operating Officers (COOs) in startups. She attributes this trend to technical founders remaining in CEO roles longer and the growing importance of product leadership. This segment explores the factors driving the need for COOs, including the rise of product-led growth and the demand for cross-functional coordination.
"publishing that after the session and then afterwards we'll have allison join one of the tables if you use the breakout tables there before we went into general session she'll be joining a table so yo..."
In this segment, Allison elaborates on the evolving nature of the COO role, identifying four key trends that necessitate the hiring of COOs. She emphasizes the importance of non-technical skill sets, such as cross-functional coordination and change management, in today's fast-paced SaaS environment. This discussion highlights the multifaceted responsibilities that COOs must navigate.
"amazing at this please submit questions as we go so one of the, things, that, we, did, is, we, had something like 500 questions alice and i reviewed the list we synthesized a bunch of them and coalesc..."
Allison introduces a framework for understanding the different types of COOs based on the intensity of support needed by founders. She categorizes COOs into four types, starting with the Chief of Staff role, which serves as an extension of the founder for project management. This segment sets the groundwork for a deeper exploration of COO roles and their specific functions.
"website so allison incredible pedigree can't tell you how excited we are to have you on red point office hours um and just to give everybody a little bit of context we were catching up a couple weeks ..."
Continuing her framework, Allison describes the Operations Lead COO, who addresses misalignment within leadership teams. This COO type focuses on enhancing cross-functional organization and managing objectives and key results (OKRs). This segment highlights the operational challenges that startups face and the strategic role COOs play in overcoming them.
"result it's extremely rare to hear about a founder being replaced by someone who a decade ago might have been called a professional ceo quote unquote dirty word these days [Laughter] yes i mean like s..."
Allison Pickens discusses the changing landscape of COO roles, highlighting the ambiguity surrounding the title and the various types of COOs that exist today. She identifies four distinct types of COOs based on the level of support founders seek, emphasizing the importance of understanding these roles in the context of scaling a business.
"scale the gtm but and so that leads me to my next question which is you know 10 or 15 years ago you you might, have, seen, a lot, of, cfo, slash, cos but today there are lots of different kinds of ceo..."
In this segment, Allison outlines the first two types of COOs: the Chief of Staff and the Operations Lead. She explains how the Chief of Staff supports founders by managing special projects, while the Operations Lead addresses misalignment within leadership teams, enhancing cross-functional organization and strategic alignment.
"intensity of support that the founder is looking for um and i think each type is prompted by a different gap that the founder might notice um the first type the lowest intensity type i would consider ..."
Allison introduces the Chief Journey Officer role, often known as the Chief Revenue Officer, which focuses on managing the customer journey from marketing to sales. She also discusses the most intensive COO role, which involves running the business and allowing the founder to concentrate on product development and vision.
"helping to set the priorities for the company and create some glue across functions and the third type of coo that i notice is um a type that i'll call the chief journey officer which more commonly co..."
This segment delves into how founders can determine the type of COO they need based on their specific challenges. Allison emphasizes the importance of understanding the level of involvement and support required from a COO to effectively scale the business.
"i think the question really becomes as a founder or ceo where do you need help that's fascinating it's it's definitely i mean it's it's a very interesting access that you raise which is the the amount..."
Allison shares real-world examples of successful COOs, such as Christina Kosmowski and Erica Schultz, who transitioned into roles that encompass broad operational responsibilities. These examples illustrate the diverse paths COOs can take within organizations and the strategic impact they can have.
"to support me and we've definitely also seen the fourth one quite a bit where particularly with say like an infrastructure company you have a ceo who the natural role in the business is a cto and so y..."
In this segment, Allison discusses the role of General Managers in large companies and how this title is less common in startups. She explains the similarities between General Managers and COOs, particularly in the context of running business units or product lines.
"this run the biz category you often have um other c-level people who are reporting into the co type and so there's often sort of an interest in having a title like president which sounds more senior t..."
Allison outlines the timeline for hiring a COO, suggesting that the need for a Chief of Staff often arises around the Series A funding stage. She explains how this role evolves as companies grow, particularly during the transition from Series A to Series B, when establishing a go-to-market strategy becomes crucial.
"awesome that's a fantastic rubric okay so we've got four different kinds of ceos now the big question is when do i hire one and which is the right one for me definitely so you know i think um in the e..."
This segment focuses on the potential for a Chief of Staff to transition into a Chief Journey Officer role. Allison discusses the skills and experiences that enable this leap, emphasizing the importance of generalist abilities and the capacity to build functional areas within the organization.
"to market leader which um you could consider to be a like the chief journey officer type that third type that i that i mentioned but of course you know series a series b this person is not managing an..."
Allison highlights the significance of trust in the relationship between founders and their COOs. She discusses how promoting from within can foster this trust and the importance of having a clear trajectory for COO roles to ensure effective delegation of responsibilities.
"of cro type for makes you on that point you know you mentioned sometimes the chief of staff becomes this cjo the customer journey officer what should we look for to know that this person can make that..."
In this segment, Allison explains the critical dynamics of the relationship between a CEO and COO. She stresses the importance of mutual respect and trust, suggesting that a COO should focus on amplifying the strengths of the CEO rather than acting as mere supervision. This partnership is vital for effective leadership.
"over time if you can prove that you can build out multiple functions and continue to lead them yourself like gain the respect of the people that you've brought onto the team you're successful in recru..."
Allison elaborates on the necessity of open communication and alignment between the CEO and COO. She likens their relationship to a 'work marriage,' emphasizing the need for trust and shared goals to foster a productive partnership. This segment highlights the importance of routines and habits that strengthen their collaboration.
"co and also as as the ceo and and i think there are two components to healthy mindset one is that there needs to be a ton of mutual respect between the ceo and the co i notice that some folks who come..."
Allison discusses the trend of promoting COOs from within the company, particularly in early-stage startups. She explains how trust and familiarity with the company's culture make internal candidates more appealing, especially when external hires may struggle to adapt to the company's dynamics.
"you shouldn't be spending your time and where you know it's helpful to have someone else come in and be a great compliment to you i think the second aspect of a healthy mindset is trust um as an examp..."
In this segment, Allison addresses the difficulties of attracting external COOs, especially in high-valuation companies with limited revenue. She explores how the disparity between a company's valuation and its actual performance can complicate recruitment efforts, making internal promotions more common.
"hired that generalist early on because this is someone again that the founder like already has faith in um i i also you know sort of positive question out there i i don't have a lot of like data on th..."
Allison shares practical tactics for ensuring alignment between the CEO and COO. She emphasizes the importance of daily check-ins and shared documentation to maintain consistent communication. This segment underscores the need for both leaders to present a united front to their teams.
"welcome feedback on this but i think it's another reason why promote from within tends to be um pretty common um what you know one other thing i'll say about like how to create um a great relationship..."
Allison discusses the key attributes to look for when evaluating COO candidates, particularly the importance of systems thinking. She explains how different functional backgrounds can influence a candidate's approach and highlights the need for a holistic understanding of the business to succeed in the COO role.
"between the two goals yeah if if you are to hire from the outside how do you do that effectively you know you need to build trust in a relatively short period of time um there's obviously going to be ..."
In this segment, Allison offers guidance to young professionals aspiring to become CEOs. She emphasizes the importance of networking with CEOs and investors, as well as building diverse skills that prepare them for future COO opportunities. This advice is crucial for navigating the ambiguous path to leadership.
"sales leaders sometimes not always sometimes are too focused on making the number this quarter and an individual transactions rather than laying the foundation to achieve a long-term revenue growth tr..."
Allison Pickens discusses the unconventional career path to becoming a COO, emphasizing the importance of creativity and networking. She highlights that aspiring COOs should focus on building relationships with CEOs and investors, as well as gaining diverse experiences across different functions to position themselves for future opportunities.
"the company's perspective evaluating a new ceo i'm a young person coming up in my career and i want to be a great ceo one day that's my career aspiration you've done it to your incredible success how ..."
In this segment, Allison Pickens outlines essential skills and experiences that can make someone eligible for a CEO role. She stresses the importance of owning revenue numbers, leading various go-to-market functions, and understanding the strategic direction of the company to prepare for future leadership roles.
"a predictable career path to get to coo so when folks say oh like i want to be coo one day um it's it's it might be a little bit like saying oh i want to start a company someday right it's like yeah l..."
Allison shares insights on how COOs can evaluate their effectiveness in supporting the CEO. She discusses the importance of trust, alignment on priorities, and the ability to complement the CEO's efforts, emphasizing that self-evaluation becomes more complex as one ascends in their career.
"yourself right so like the vcs build these exact networks they can place you in ceo roles of their portfolio companies you get no headhunters who recruit for these folks um there are a lot of them act..."
In this segment, Allison Pickens elaborates on the day-to-day self-evaluation for COOs. She emphasizes the need to meet current targets while also laying the groundwork for future success, ensuring alignment with the company's long-term mission and objectives.
"over time um not just growing up in one career path but showing that you can lead a team in sales and in marketing and customer success right i don't think you necessarily need all three of those area..."
Allison discusses her transition from COO at Gainsight to her current role as an advisor and investor for B2B SaaS companies. She explains how her background in operations and go-to-market strategies allows her to effectively support CEOs in achieving their business goals.
"as a ceo when do you know that you're doing a good job it's a it's a great question and i think um actually there's some ambiguity here too which is probably a signal of the importance of the role rig..."
Allison highlights the significance of hiring a revenue operations leader to enhance a CEO's leverage. She explains how this role can provide a unified view of the customer journey and ensure consistent processes across functions, ultimately driving better customer experiences and monetization.
"most important thing is are you complementing your ceo effectively so you know um are you satisfying the equation one plus one equals three are you dividing and conquering appropriately or are you ove..."
In this segment, Allison addresses the organizational structure of customer success and support roles within a company. She discusses the potential benefits of having a Chief Customer Officer and how this role can effectively manage customer success, professional services, and support functions.
"different time horizons am i meeting my targets today am i laying the groundwork to meet my targets next year am i laying the foundation to fulfill my company's purpose like mission statement long ter..."
Allison reflects on her varied responsibilities as COO at Gainsight, sharing insights on how she adapted to different roles over time. She emphasizes the importance of complementing the CEO's efforts and being proactive in identifying and filling gaps within the management team.
"director in order to formalize relationships um so i don't consider myself to be a vc or you know solo capitalist is also a term that has become um popular uh you know i will always be an operator fir..."
Allison discusses the critical role of the Chief Customer Officer in managing customer success and support. She explains how this role can enhance customer experiences and drive growth, particularly in companies with a strong focus on customer-centric strategies.
"valuable to hire to allow a ceo to increase their leverage does the ceo have their own coo oh that the ceo can hire question um i've noticed that uh the business operations role or um increasingly i t..."
In this segment, Allison addresses how the responsibilities and skills of a COO evolve over time. She emphasizes the need for COOs to adapt to changing business needs and to continuously seek ways to add value to the organization.
"across the journey so yeah i'd say like probably most leverage you can get is hiring a rev-ops person awesome okay nick from brazil who's an old friend asks i'm curious about the trade-offs of custome..."
Allison Pickens discusses her diverse responsibilities as COO at Gainsight, highlighting her involvement in sales, customer success, and business partnerships. She emphasizes the importance of complementing the CEO's efforts and adapting to the company's needs, showcasing the dynamic nature of the COO position in scaling a business.
"ways so you know at the time i was i was doing everything right it was like a like very generalist kind of thing i was selling and building sales ops like lead finance and hr and then within a few mon..."
In this segment, Allison explains how a COO must align with the CEO's priorities and the company's stage of growth. She shares insights on how to effectively support the CEO and fill gaps within the management team, emphasizing the strategic partnership between the COO and CEO in driving company success.
"you know the the most important aspect of the cool role is that they complement what the ceo is doing and you know nick and i would have many conversations over the years where we talk about what are ..."
Allison recommends key books for aspiring COOs, focusing on leadership development and emotional intelligence. She highlights the importance of self-directed learning in leadership roles and suggests titles that provide resilience strategies and insights into effective leadership styles, including Ben Horowitz's 'The Hard Thing About Hard Things' and Eckhart Tolle's 'A New Earth.'
"awesome okay nathan asked the most popular or most upvoted question with 39 upvotes and we talked a little bit about this before if you were to recommend three books for aspiring cos which books would..."
Allison emphasizes the significance of emotional intelligence in leadership, advocating for a servant leadership approach. She discusses how understanding one's impact on others and adapting leadership styles to individual needs can enhance team dynamics and foster a positive work environment.
"you know like non-violent communication i think is a really interesting one and i can probably post this to my linkedin likes you know some of my favorite books in that category i also um i'd make a p..."
In this segment, Allison shares strategies for aspiring COOs to find mentorship and guidance. She suggests leveraging connections within the tech community and emphasizes the value of learning from colleagues and peers, encouraging proactive engagement to enhance leadership skills.
"awesome a couple of um so in addition to reading mentorship is really important is there a way of is there are there's a community of cos or is there a sort of a path to finding a mentor that you've s..."
The session concludes with reflections on the insights shared by Allison Pickens regarding the evolving role of COOs. The discussion highlights the importance of understanding company needs at different stages and the value of mentorship and continuous learning in leadership development.
"awesome well that's all the time we have for today for questions allison i i just think the thing that stuck with me the most from this conversation was your hierarchy of different cos and i think wha..."