20 Sales Notion's CRO Olivia Nottebohm on How To Build Great Operations at Your Company, How To Use The Trust Equation in Hiring, How To Do Referencing Most Effectively and Whether To Fill Seats or Wait for the Perfect Hire

In this episode of "20 Sales," host Harry Stebbings interviews Olivia Nottoborm, Chief Revenue Officer at Notion, who shares her journey from McKinsey to leading sales and operations at tech giants like Google and Dropbox. Olivia discusses the importance of operational rigor, customer-centric strategies, and the need for companies to remain agile and innovative in the tech industry. She also emphasizes the significance of building a world-class team, maintaining high hiring standards, and fostering a culture of internal growth and opportunity. Additionally, Olivia highlights the value of trust and direct communication in leadership roles, and the delicate balance of making data-informed decisions while being open to intuition. The conversation also touches on the challenges of hypergrowth and the necessity of strategic focus to avoid becoming sidetracked by less promising business segments.

• Harry Stebings hosts the 20 Sales podcast, which focuses on insights from top sales leaders.
• The show aims to provide tips, tactics, and strategies for scaling sales organizations.
• Olivia Nottebohm, Chief Revenue Officer at Notion, is the guest for the episode.
• Olivia has an extensive background with experience at Dropbox, Google, and McKinsey & Company.
• Acknowledgments are given to individuals who contributed to the episode, including Danny at Sequoia and Akshay and Camille at Notion.

"Today we're joined by a great I'd heard so many incredible things from many different people and so I was so thrilled to welcome Olivia Nottoborm, chief revenue officer at Notion, where she leads the sales, marketing, customer success and customer experience teams."

The quote introduces Olivia Nottebohm and her role at Notion, setting the stage for the conversation about her experiences and insights in tech and sales.

• Salesoft is highlighted as a leading sales engagement platform.
• The platform helps sales teams increase revenue and provides insights for performance coaching and deal management.
• Salesoft is endorsed by major companies like IBM, Shopify, and Stripe.

"Salesoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace."

The quote explains the purpose and value proposition of Salesoft, emphasizing its role in modernizing sales processes.

• Pipe is presented as a financing solution for businesses with recurring revenue.
• It allows companies to turn their recurring revenue into upfront capital quickly and without dilution or restrictive terms.
• Pipe supports various industries and offers a promotional deal for 20 Sales listeners.

"Pipe is a completely new way to finance growth without taking on restrictive loans or diluting your ownership."

The quote describes Pipe's unique approach to financing, offering an alternative to traditional loans or equity financing for businesses.

• Copper CRM is described as a flexible CRM solution for Google workspace businesses.
• It integrates with Google apps and is user-friendly, requiring minimal training.
• Copper CRM offers a discount for 20 Sales listeners on any annual plan.

"Copper is a dramatically different kind of CRM built for Google workspace businesses."

The quote introduces Copper CRM as a CRM solution specifically designed for businesses using Google workspace, emphasizing its ease of use and integration.

• Harry Stebings welcomes Olivia Nottebohm to the podcast.
• Olivia expresses her pleasure in joining the show.

"Well, it's lovely to be here, Harry. Thank you for having me."

Olivia Nottebohm's response to the welcome, indicating she is pleased to participate in the podcast.

• Olivia discusses her attraction to the tech industry's fast pace and innovation.
• She mentions her early career at McKinsey and her fascination with Moore's law.
• Olivia values the challenge and continuous learning in the tech sector.

"Tech has always been something that, for me, was this fast moving pace that I adored so early on."

The quote captures Olivia's passion for the dynamic and innovative nature of the tech industry, which drew her into the field.

• Olivia shares the casual nature of her introduction to Notion through mutual connections in Silicon Valley.
• She discusses her experience at Google Cloud and the importance of acquiring digital natives for future enterprise growth.
• Olivia's conversation with Ivan and Akshay at Notion led to her joining the team.

"And at one point Ivan and Akshay said, hey, do you want to come join the team? That's how it happened."

The quote recounts the informal yet pivotal moment when Olivia was invited to join Notion, highlighting the serendipitous nature of career opportunities in Silicon Valley.

• Olivia reflects on her takeaways from Google, including the company's operating rigor and customer-centric approach.
• She admires the auction model for ads and the operational excellence that drives Google's success.
• At Google Cloud, customer focus was key to convincing the world of Google's enterprise capabilities.
• Diane Green's leadership at Google Cloud and her customer-centered staff meetings are highlighted as influential.

"What really wowed me at Google was the operating rigor. It is not an accident that they perform as well as they perform and it's a high bar that's held."

The quote emphasizes the deliberate and disciplined operations at Google that contribute to its high performance, illustrating the importance of operational rigor in successful companies.

• Olivia explains that great operations involve connecting functions within a company to work seamlessly together.
• She stresses the importance of anticipating and removing blockers to ensure smooth progress across teams.
• Olivia sees her role as ensuring that leaders in marketing, sales, customer success, and operations are aligned and unblocked.

"Ops is really about connecting end to end, how functions work together."

The quote defines operations as the coordination and integration of various functions within a company, highlighting the strategic aspect of anticipating and addressing potential obstacles.

• Olivia advises against making decisions solely to optimize for revenue.
• She suggests removing elements that might lead to revenue-centric decision-making.
• An example is provided to illustrate the importance of not allowing revenue optimization to dominate strategic decisions.

"You never want to make decisions as you're building to optimize for revenue."

The quote underlines Olivia's philosophy that while revenue is important, it should not be the sole focus when making decisions, emphasizing a more holistic approach to business growth.

• Companies often start with multiple business drivers, but over time, some areas may not present enough total addressable market (TAM) to sustain significant growth.
• Growth is paramount in business, particularly when aiming to double revenues consistently.
• It's important to avoid distractions from parts of the business that cannot keep up with the desired growth rate.
• Sunsetting a business area can be a strategic decision to prevent resource dilution and maintain focus on more promising growth areas.

"But over time, it's clear that there's just not enough tam there. There's not enough opportunity there to actually sustain that being the business driver for the company."

This quote highlights the realization that not all early business drivers have the potential to sustain long-term growth, which is a critical factor in strategic decision-making.

• There is a convergence of different parts of the sales funnel, with customer success, marketing, and sales overlapping more than before.
• The educated nature of buyers today means marketing plays a larger role in the sales funnel.
• Attribution in this intermingled environment involves isolating the impact of different teams on outcomes such as net new visitors and sign-up rates.
• Teams need to work cohesively yet be able to attribute success to either marketing efforts or product and web improvements.

"The brand team, the top of the funnel team is owning net new visitors. They are obviously working in concert with product to drive sign up flow, right."

This quote explains how different teams are responsible for specific parts of the funnel and must work together while still being able to attribute successes to the right efforts.

• A flat management structure can be effective, with leaders managing a comfortable number of direct reports without micromanaging.
• Effective leadership involves coordinating across roles and thinking strategically rather than owning a specific piece of work.
• Communication with direct reports is crucial and can take various forms, including weekly meetings, shared Slack channels, and one-on-one check-ins.

"I do believe in more of a flat structure. So a span of control of eight, I feel is very comfortable, especially in my role, where I'm really not trying to do the job of any one of the functional leaders on my team."

This quote emphasizes the speaker's preference for a flat management structure and the importance of not micromanaging but rather facilitating strategic coordination.

• Regular communication with direct reports is essential, including weekly leadership meetings and one-on-one interactions.
• Using structured documents and tools like Notion can help keep one-on-ones focused and productive.
• Addressing concerns with direct reports involves a supportive approach, asking how they are feeling, identifying challenges, and offering help.

"The very, very tough conversation kind of of, hey, you've kind of really hit a wall, comes from me in the form of checking in on them and seeing how they think they're doing."

This quote explains the approach to tough conversations with direct reports, focusing on self-assessment and offering support rather than criticism.

• There should be a high bar for bringing in external talent, especially if the existing team is high caliber and the business is in a growth phase.
• Internal promotions can motivate team members by showing them there are opportunities for career advancement within the company.
• When a new external hire is necessary, it's important to communicate the reasons and still focus on the development and success of internal team members.
• Reminding team members that the scope and challenge of their roles naturally expand with the company's growth can help maintain motivation.

"There has to be a very high bar for bringing in external talent. If you have a high caliber team, especially when you're growing a business and especially when you're trying to be innovative, you do want to give people a chance to shine and try things that maybe they haven't tried before."

This quote stresses the importance of setting a high standard for external hires and the value of providing growth opportunities to existing team members.

• The importance of balancing kindness with directness in decision-making is emphasized.
• Empathy and understanding of personal experience are crucial to relate to others during tough decisions.
• The right answer for the business should be discussed openly, considering the human element involved.

"So we have a value at notion that I feel very, very resonant with, and it's be kind and direct. If you pair the two, you are better off."

This quote highlights the company value that promotes a balanced approach to decision-making, combining kindness with directness to achieve optimal outcomes.

• Recognizing and absorbing pressure is a key part of leadership.
• Leaders should provide their teams with the space to operate and not transfer their anxiety.
• Personal habits, like running, can help maintain a calm and focused state.

"Part of what you're signing up to is absorbing the pressure that is part of your function."

Olivia explains that a leader's role includes managing and internalizing pressure rather than passing it onto the team, which is crucial for effective leadership.

• Interviews are prone to false positives and less likely to false negatives.
• References are critical, especially from those not provided by the candidate.
• A thorough reference check can reveal if a candidate is a pressure absorber or a pressure transferrer.

"I view interviews as highly, highly likely to get a false positive, less likely to get a false negative."

Olivia notes that interviews can be misleading, and emphasizes the importance of conducting thorough reference checks to truly understand a candidate's capabilities and tendencies, such as being a pressure absorber.

• The process of reference checking should be thoughtful and thorough.
• It's important to reach out to a candidate's network beyond the provided references.
• The aim is to ensure that the person being hired will be a positive addition and not tarnish the referrer's reputation.

"I know that I will be more effective in my reference checking if I can actually talk to someone who feels like actually, if I hire this person and they're a bad egg, they will feel like their own brand is tarnished because they told me that they were stellar."

Olivia describes her strategy for reference checking, which involves speaking to people who have a vested interest in maintaining their reputation, thereby ensuring they provide honest feedback about the candidate.

• Establishing context and rapport is key before discussing a candidate's weaknesses.
• Asking for weaknesses in a way that acknowledges imperfection can lead to more honest responses.
• Reference checks should be seen as an investment of time for valuable insights.

"What would be the one thing that exhibits as something that you're like, no one's perfect. This is the thing. I just need to navigate around with this person."

Olivia shares her approach to gently uncovering a candidate's weaknesses by framing the conversation around the idea that no one is perfect, encouraging the reference to share candidly.

• Acknowledging flags during the reference check is crucial.
• Overconfidence in one's ability to coach through issues can lead to mishires.
• The importance of not rushing hires due to necessity is emphasized, especially with a high talent need.

"And I would say 2022 will be a very challenging year globally in the world of talent."

Olivia reflects on the challenges in the hiring landscape and the lessons learned from past mishires, stressing the need for patience and thoroughness in the hiring process despite talent shortages.

• Hiring is a team effort, and everyone should be involved in sourcing candidates.
• Maintaining high hiring standards is key, even in a challenging talent market.
• Relationships and referrals are crucial for finding great candidates.

"And we have this referral tournament, and we have a lot of great refers from functions who have nothing to do with functions that are being hired for."

Olivia discusses the importance of leveraging the entire company's network for referrals and maintaining a high hiring bar, even when talent is scarce.

• The CEO's high emotional intelligence (EQ) is valued and beneficial in the hiring process.
• The CEO's involvement in interviews is seen as a testament to the company's commitment to culture and hiring standards.

"That is, he has such incredible high EQ. It's just a gift, honestly, to have a CEO with such incredible Eq."

Olivia praises the CEO's EQ and his involvement in the hiring process, highlighting the positive impact it has on maintaining company culture and standards.

• Trust is the foundation of a strong relationship between the Chief Revenue Officer (CRO) and CEO.
• The trust equation is a formula that includes credibility, accessibility, and reliability as key components.
• Building trust can be approached algorithmically, reflecting Olivia's analytical background.

"I actually believe in the trust equation."

Olivia briefly mentions her belief in a structured approach to building trust in professional relationships, specifically between the CRO and CEO.

• Credibility, accessibility, dependability, and self-interest are key components of trust.
• A person's trustworthiness is diminished if they are perceived to be acting solely in their own self-interest.
• Aligning with the greater good and being a team player are essential for maintaining trust.

"If someone engages with you and they're highly credible, they're highly accessible and they do what they say they're going to do, but it's very clear that they're always in it for themselves and only themselves. You do tend to have a lower trust of that individual."

This quote emphasizes the negative impact of self-interest on trust, even when other factors like credibility and dependability are present.

• Hyper-growth companies, defined as those growing over 60%, have a significantly higher chance of reaching $1 billion in revenue.
• Only a small percentage of hyper-growth companies can maintain their growth rate past $100 million ARR.
• The difficulty of sustaining rapid growth is a serious challenge and responsibility for business leaders.

"Only 15% of companies who are growing at over 60% as they reach 100 million ARR are able to maintain that growth."

This statistic illustrates the rarity of sustained hyper-growth in companies, highlighting the challenge of scaling businesses successfully.

• Olivia considers herself a world-class operator, skilled at uniting teams to achieve goals.
• She acknowledges a potential weakness in being overly analytical and stresses the importance of trusting one's gut in decision-making, especially in a hyper-growth environment.

"I do think I'm a world class operator. I do love bringing teams together and making sure that we are just knocking it out of the park."

Olivia expresses confidence in her operational abilities and her passion for team collaboration.

• Decisions should be defensible and understandable to the entire company.
• Popularity should not drive business decisions; rather, they should be based on solid rationale.
• Inconsistent or opaque decision-making can lead to problems in recruiting and team motivation, particularly during rapid scaling.

"You always have to have a rationale that you can stand up in front of an entire company and explain."

This quote underlines the importance of transparency and justifiable reasoning behind business decisions, especially as a company grows.

• Olivia shares a personal anecdote about changing her mind regarding her children's activities, reflecting the broader principle that personal experiences should not dictate others' paths.
• Professionally, she believes in making decisions that can be explained and defended to the entire team, avoiding the pitfalls of popularity-driven choices.

"Just because I grew up playing pond hockey does not mean that my California kids need to do the same."

Olivia uses a personal example to illustrate the idea that one's preferences should not necessarily be imposed on others, a concept applicable in both personal and professional contexts.

• Sales Loft and Pipe are mentioned as valuable tools for sales teams and businesses seeking growth.
• Sales Loft is highlighted as a leading sales engagement platform, while Pipe is noted for providing non-dilutive growth capital to companies with recurring revenue.
• Copper is introduced as a CRM solution that is flexible and integrates seamlessly with Google Workspace.

"Sales loft is the leading sales engagement platform, helping sales teams drive more revenue."

This quote points to the significance of having effective tools to support sales teams in driving business growth.

"Pipe is a completely new way to finance growth without taking on restrictive loans or diluting your ownership."

The quote explains the innovative approach Pipe offers for financing, which is advantageous for businesses with recurring revenue streams.

"Copper is a dramatically different kind of CRM built for Google workspace businesses."

This quote introduces Copper as a CRM solution tailored for businesses that use Google Workspace, emphasizing its versatility and ease of use.