Mark Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241

Intro (0s)

• Founders should not create the playbook themselves, but they often wait too long to hire a go-to-market team, possibly due to concerns about finding a good salesperson without sufficient traction (6s).
• A common mistake during the transition to the next phase is not increasing prices to a point where friction is encountered (16s).
• Mark Plank has been interested in sales since he was in fifth grade, selling wrapping paper, and has continued to be involved in sales throughout his life, including selling hot tubs and appliances in college (58s).
• Mark believes that while some people may be naturally inclined towards sales, it is also a skill that can be learned, and that having a competitive attitude and being okay with losing are important qualities for a salesperson (1m38s).
• Mark thinks that it's essential for salespeople to be able to handle rejection and bounce back from losses, as even the best sales reps have win rates of 15-40% (2m40s).
• Mark disagrees with the idea that it's not okay to be good with losing, instead believing that as long as losing motivates you, it's acceptable to experience rejection in sales (2m34s).
• Mark and the host discuss the importance of having a strong competitive drive and a hatred for losing, but also being able to accept rejection and move forward in sales (2m28s).

Why Are Win Rates So Low in Sales? (3m8s)

• Win rates in sales are typically low, ranging from 15 to 20%, with the majority of losses attributed to indecision, where potential customers choose to stick with their current solution rather than making a change (3m25s).
• In many cases, indecision is due to the sales team's inability to articulate the solution effectively or prove enough value in the product or service being sold (4m22s).
• However, there are also valid reasons for indecision, such as changes in company priorities, budget constraints, or personnel changes, which can be beyond the sales team's control (4m34s).
• The best sales representatives understand the importance of maintaining relationships with both won and lost customers, as these connections can lead to future opportunities and a faster deal cycle (4m57s).
• It's essential to handle rejection graciously and maintain a positive relationship, even when a deal is lost, as this can lead to a "circle back loop" of potential customers who may be ready to make a decision in the future (5m33s).
• Building a pipeline of potential customers who have been engaged with in the past can lead to a steady stream of opportunities and help to increase win rates over time (5m37s).

Is It Easier to Sell Replacement Products or Net New Solutions? (5m40s)

• Selling a replacement product is generally easier than selling a net new solution, as it involves replacing an existing line item in a financial model, expense page, budget, or existing system (5m41s).
• When selling a replacement product, the budget for the existing system already exists, making it easier to close the deal by beating the competition (5m52s).
• In contrast, selling a net new solution requires creating a new category or budget for a product that doesn't exist, which involves going through various additional steps and considerations (5m57s).
• The difficulty of selling a net new solution is exemplified by the experience of selling an e-signature solution at EchoSign, where some customers would opt to stick with paper-based processes despite the evaluation process (6m13s).
• At Rippling, the focus is on replacing existing systems, which is found to be a more straightforward process, as the customer is already looking to switch and the goal is to win the deal by beating the competition (6m29s).

Is Outbound Sales Dead? (6m44s)

• Outbound sales is often misunderstood and considered dead, but this notion is likely due to indecision, ghosting, or ineffective outbound strategies (6m44s).
• People who claim that outbound sales is dead are either trying to provoke a reaction or are not skilled at scaling large businesses (7m4s).
• Building a business without outbound sales is challenging, as relying solely on marketing form fills, programmatic email, or other methods is not enough (7m32s).
• In the early days of Rippling, not pushing outbound sales harder was a significant mistake, despite having a strong marketing team that generated thousands of inbound demos every month (7m45s).
• Rippling eventually reached a crisis point where they had to quickly build an outbound team from scratch to meet growth rate needs, which was a stressful but necessary step (8m1s).
• Outbound sales is harder and different, but it is not dead, and companies need to adapt to scale and grow (8m23s).
• Rippling's SDR org books over 1,000 outbound demos a month, with 50% of them booked over the phone, demonstrating the effectiveness of outbound sales when done correctly (8m30s).

How To Build an Effective Outbound Function (8m40s)

• Building an effective outbound function requires a deep partnership with marketing, where both teams work together to generate pipeline and credit is given where due, regardless of whether the lead is inbound or outbound (9m13s).
• A strong partnership between marketing and sales is crucial, and this can be achieved by having a culture that encourages collaboration and shared goals, often set by the CEO (11m14s).
• Marketing should be financially incentivized to contribute to the sales process, such as by receiving part of the commission when a new customer is acquired (11m8s).
• To build an effective outbound function, it's essential to have a strong understanding of who to reach out to and when, which can be achieved by capturing intent data from various sources, such as website visits, review sites, and LinkedIn (10m15s).
• Marketing should curate this intent data and provide it to the sales team, along with effective messaging and sequencing, to help drive outbound success (10m30s).
• The sales team should be responsible for ruthless execution of daily-driven KPIs, while marketing provides critical support and guidance (10m49s).
• Having a strong partnership between marketing and sales can help prevent blame-shifting when revenue targets are missed, and instead encourages collaboration to achieve shared goals (11m41s).
• It's essential to acknowledge and give credit to marketing when they contribute to the success of an outbound function, rather than taking all the credit for oneself (11m54s).
• Hiring experienced professionals, such as Ashley Kelly, can also be crucial in building an effective outbound function (8m56s).
• The marketing team has a pipeline plan that they sign up for, with goals focused on generating pipeline rather than just tracking webinars and content downloads (12m5s).
• The company has a top pipeline number, which is revenue, and this number is set by Parker, the CEO, who determines the growth rate needed to continue being an outlier in the market (12m28s).
• The planning process involves a detailed and ruthless examination of 50 different sub-segments, including SNB, midmarket, Enterprise, channel sales, and product sales, to determine capacity plans and quotas (13m11s).
• The company starts by making reasonable assumptions about growth and then determines what is attainable, and then identifies the gap between the attainable plan and the desired plan (13m43s).
• To close the gap, the company identifies 10-15 different levers that can be pulled, such as hiring more reps or generating more demos (13m59s).
• The pipeline number is broken down into segments, but the approach depends on the stage of the company, with early-stage companies focusing on who they are getting demos from and building segmentation around that (14m34s).
• As the company grows, the sales team branches off and becomes more specialized, with the CRO's role changing to focus more on sales operations (14m57s).
• The CRO's role transitions from closing deals to overseeing sales operations and managing the sales team, with a focus on strategy and planning (15m8s).
• To build an enterprise sales machine, operational planning is crucial, which involves analyzing past performance in different segments to identify areas for improvement (15m14s).
• The goal is to determine the revenue target and then create a top-down plan to achieve it, without being too concerned about specific revenue from each segment (15m34s).
• The top-down plan is based on the number of demos expected in each segment and the number of people needed to staff those segments (15m42s).
• Parker, presumably a key decision-maker, focuses on the overall revenue target and leaves it to others to figure out how to achieve it (15m33s).
• The planning process involves slotting in the right people against different segments to maximize performance (15m27s).

Close Rates Across SMB, Mid-Market & Enterprise Segments (15m45s)

• The company sells to a wide range of customers, from small businesses with 3-4 employees to large enterprises with up to 5,000 employees, with a close rate of 50-60% on the low end of the market and 15% on the high end (16m7s).
• The company has segments based on employee size, but also has multiple products, with 30 different products, which led to the creation of separate product account executive teams, resulting in 50 segments (16m44s).
• The close rates vary across segments, with SMB at 50-60%, Mid Market at around 20%, and Enterprise at around 15% (17m19s).
• The company measures win rates from different stages, with a lower win rate when measuring from the initial demo stage, but a higher win rate when measuring from a later stage, such as after a second call has been scheduled (17m56s).
• The company uses inbound sales for small businesses with 3-4 employees, but uses outbound sales for mid-market and enterprise segments, with different teams handling different size ranges, including 50-250 employees, 250-1,000 employees, and 1,000-5,000 employees (18m49s).
• The company's average contract value (ACV) size is a factor in determining whether to use outbound sales, with smaller ACVs not justifying an expansive outbound model (18m23s).
• Rippling's business model involves buying a seat for every single person in the company, with an average price per employee per month (pepm) of $60-$70 across the customer base, and an average deal size of $45,000 for mid-market companies with 50-250 employees (18m59s).
• The sales cycle for mid-market companies typically lasts around 50-60 days, with some deals closing in as little as a month and others taking up to three to five months (19m47s).
• Building an outbound sales strategy is feasible with a $45,000 average deal size, and customer success is also justified at this price point (20m7s).
• Initially, Rippling had a customer success team that focused on making customers successful and renewing contracts, but not selling new products (20m18s).
• As the company grew and expanded its product offerings from three to over 30, the customer success model became unsustainable, and the company converted to an account management team (20m53s).
• The account management team is responsible for owning the commercial relationship, renewals, and ensuring customer success, while also being held accountable to a quota (21m36s).
• New logo sales reps pass deals over to account managers, who focus on the commercial relationship and customer success, rather than just support (21m48s).

Is Customer Success Overrated in Enterprise Sales? (22m5s)

• The concept of customer success in enterprise sales is debated, with some arguing it is overrated, citing the example of Chris Dagnan at Snowflake who views customer success as less important than professional services or customer support (22m16s).
• For multi-product companies, it is challenging to have both customer success managers and account managers, as it can create conflicting priorities and incentives (22m35s).
• At Rippling, account managers own the commercial relationship and focus on expanding usage within the product suite, while technical account managers focus on product adoption, success, and retention (22m46s).
• The company also has a support team that responds to urgent issues, and it is believed that having a sales DNA at the core of account management is essential for understanding and caring about customer success (23m7s).
• Incentivizing account managers is crucial, and at Rippling, the compensation plan was changed to tie 70% of the incentive to selling new business and 30% to retention, specifically dollar retention (24m6s).
• This change led to a significant improvement in churn metrics, and it is believed that owning both new revenue and retention is essential for success in enterprise sales (24m21s).
• The approach to customer success and account management may vary depending on the company's size and market, with high-velocity companies potentially requiring different strategies (23m54s).
• Initially, Rippling's account managers only had a new revenue quota, but this approach was later changed to include a retention number, as it was realized that incentivizing retention was necessary (23m36s).

How Matt Approaches Discounting in a Competitive Landscape? (24m30s)

• Discounting is viewed as a completely made-up concept, as the only thing that truly matters is the net price, which is the final amount paid after any discounts are applied (24m44s).
• The list price is considered a "fake price" that doesn't matter, as it's the net price that customers care about, and discounting is simply a factor of where the list price is set (25m9s).
• List price refers to the initial price shown to customers, which may be displayed on a company's website, especially for SMB and down-market businesses with self-served signups and trials (25m27s).
• Net price is the actual price point targeted, which may be lower than the list price, depending on factors such as the size of the company, the number of products purchased, and the timeline for implementation (25m56s).
• A consistent and firm discount policy is essential to avoid having reps make up their own prices, and to ensure that customers understand the pricing structure based on factors such as the deal timeline and the amount of products purchased (26m32s).
• Having a clear discount policy in place helps to address situations where customers may compare prices with others, as it allows the company to walk them through the policy and stand behind it (27m25s).
• A well-structured discount policy prevents a "wild west" scenario where reps can make up their own prices, which can quickly get out of control (27m37s).

Are Logos or Early Wins More Important for Startups? (27m42s)

• When a startup is in its early stages, the only thing that matters is winning customers, regardless of the revenue or the customer's logo, as it validates that the product can be charged for and that customers will buy it (27m42s).
• Founders often make the mistake of trying to maximize the revenue of one specific deal, instead of signing up as many customers as possible, even if it means offering a lower price (28m35s).
• As a startup grows, it's essential to increase prices to a point where there is friction, meaning some customers may walk away due to the higher cost, as this indicates that the price is high enough (28m51s).
• High win rates, such as 60-70%, can be a sign that the price is too low or that the startup is not in enough deals, and founders should aim to raise prices until they reach a point where they start to lose deals (29m11s).
• The ideal price point is found by gradually increasing prices over time until some customers start to express concerns about the cost, and it's essential to lock in existing customers at their original price to maintain their loyalty (29m52s).
• Raising prices by 20% may lead to a slight decrease in win rates, but it can result in significantly more revenue over time (30m41s).

Approaching Multi-Year Contracts (30m50s)

• Multi-year contracts are important, and incentivizing sales teams to sell them can be beneficial, with a kicker in the compensation plan for selling multi-year deals, which should be relative to the commission rate, around 10-15% of the deal (31m10s).
• The kicker should not be too high, as it can disrupt the commission rate, and it's generally recommended to keep it around 10-20% of the original contract or commission rate (31m56s).
• Discounting in price can be a way to instill urgency in deals, but it's essential to understand the customer's timeline and needs before offering discounts (32m21s).
• A common mistake is offering time-based discounts without understanding the customer's ability to move quickly, which can lead to a terrible experience for both parties (32m36s).
• To instill a sense of urgency, it's crucial to understand the customer's ideal timeline upfront, which can be done by asking about their pain points and ideal implementation timeline (33m2s).
• Building trust with the customer and making them aware of the competitive pricing can also help create a sense of urgency and encourage them to make a decision (33m51s).
• Time-based discounts are often counterproductive as they create a sense of urgency that may not be genuine, and people tend to sign contracts at the end of the month or quarter due to the relationship built throughout the valuation process, rather than the discount itself (33m59s).
• Deal reviews are essential to ensure that salespeople, who are often optimistic, have a solid understanding of the deal and have asked the necessary questions to verify the information (34m55s).
• The primary goal of deal reviews is to ask questions that poke holes in the salesperson's assumptions and create a relationship where the salesperson feels comfortable providing detailed information (35m29s).
• Deal reviews should involve asking questions such as who the decision-makers are, who the salesperson is talking to, and what the timeline is, to gain a deeper understanding of the deal (35m31s).
• Pipeline reviews should be conducted regularly, ideally every week, and involve managers and salespeople in a one-on-one setting to ensure that deals are thoroughly reviewed and understood (36m15s).
• Deal reviews should not be conducted in large groups, as this can be time-consuming and ineffective, but rather in smaller settings where detailed discussions can take place (36m37s).

An Acceptable vs. Unacceptable Reason for a Deal to Slip (36m43s)

• When evaluating whether a deal has slipped for an acceptable or unacceptable reason, it's essential to consider the historical tendency of the sales representative, as deals often push in sales, and determine if the rep normally closes deals within the expected timeline (36m54s).
• Reps may convince themselves that a deal has been delayed due to reasons like a new person joining the company or a budget issue, but in reality, they are often starting over from scratch, and time kills all deals (37m50s).
• It's crucial for reps to understand that deals can evaporate over time, and pushing deals can lead to a lower closing rate, as some percentage of deals will inevitably "poof" and disappear (38m15s).
• One of the worst reasons for a deal to slip is the legal team not completing the review on time, which can be frustrating because it seems out of the rep's control (38m30s).
• However, this issue can often be attributed to the rep not running parallel tracks, such as sending the contract for review and waiting for the vendor of choice designation, which can cause delays (39m52s).
• To avoid these issues, reps should ask about the contract processing and legal review process within the company during the evaluation phase and parallel track these tasks to ensure a smoother closing process (39m22s).
• Parker's skepticism about deals pushing and not closing is a common concern, but reps should focus on understanding the reasons behind the delay and work to close deals within the expected timeline (37m16s).

Lessons on Maintaining Morale During Volatile Times (40m6s)

• Maintaining morale in volatile times is crucial, and a key lesson is to not react poorly to rejection or failure, as it can negatively impact the team's morale (40m22s).
• As a sales leader, it's essential to "kill them with kindness" when dealing with rejection, by thanking the client for their time and expressing appreciation for their consideration, which can lead to unexpected opportunities in the future (41m8s).
• Leaving every interaction with a positive mindset can lead to unexpected opportunities and a higher chance of deals bouncing back (41m40s).
• As a sales leader, it's essential to own up to mistakes and not point fingers at team members, as it can create a negative atmosphere and undermine morale (42m10s).
• Weak or insecure sales leaders may try to deflect blame, but a strong leader takes responsibility and acknowledges their role in the team's success or failure (42m28s).
• A sales leader's job is not just to know what to do, but to get the team to execute, and they should take ownership of the team's performance and not blame others for mistakes (42m49s).
• Parker's advice is to remember that a sales leader doesn't get credit for knowing how to do something themselves, but rather for getting the team to do it, which is a key aspect of leadership (42m37s).

What’s the Weakest Part of Matt’s Go-to-Market Team & Why? (43m7s)

• Evaluating the go-to-market team reveals that the weakest part is the sales organization's lack of involvement in generating outbound demos, with sales reps relying on SDRs to schedule demos and not owning their pipeline (43m8s).
• Up until 18 months ago, the sales organization never thought about generating outbound demos, and it wasn't until the hiring of Ashley Kelly that they started to focus on outbound sales (43m30s).
• The company's culture has shifted to emphasize the importance of sales reps caring about where their pipeline comes from, but they still don't own it, with outbound SDRs owning the quota and scheduling demos (44m11s).
• It's believed that sales reps should be responsible for leads and not just rely on outbound SDRs, as this approach can become presumptuous and lead to saturation of the market (44m32s).
• The outbound sales funnel is critical, and every time a new SDR team is evaluated, there's always a part of the funnel that's broken, requiring training and fixing to increase demo output (44m54s).
• Sales reps want control over their accounts and destiny, but when given accounts, they often don't perform without structure and focus, making it challenging to manage reps doing outbound (45m36s).
• A big mistake was not empowering sales reps and SDRs to take ownership of their pitches and scripts, with the company holding on to a centralized approach for too long (46m6s).
• The company has since hired successful VPs to own different segments, and the approach has shifted to empower teams to take ownership of their pitches and scripts (46m24s).
• The company's deck and pitch were stale, and it took too long to realize that the teams should be empowered to create their own content and challenge the status quo (46m48s).
• Today, the team is more useful than the leader in terms of winning business and bringing customers on board, with a focus on empowering teams to take ownership and challenge the status quo (47m21s).

The Revenue Split Across SMB, Mid-Market & Enterprise (47m28s)

• Revenue makeup is divided among small and new business (SNB), midmarket, and Enterprise teams, with a goal of having roughly the same size teams by the end of next year, with around 60 SNB reps, 90 midmarket reps, and 40 Enterprise reps, totaling 150 reps out of 300 across the board (47m28s).
• The fastest-growing segment is the upmarket (UPM) segment, with the company moving upmarket quickly and now competing with large companies like Workday, growing at a rate of 60-90% year-over-year (48m13s).
• To maintain high growth rates, some segments need to grow at 200-300%, with the UPM teams currently growing the fastest (48m35s).
• International growth is not happening as quickly as desired, with challenges in replicating the US market's organic, brand, and free benefits, making it harder to efficiently acquire leads (48m48s).
• International teams are in place, including in Dublin and Sydney, but the company is still trying to find the right approach, with potential for explosive growth once the right strategy is found (48m51s).
• Entering new markets is more expensive, and as the company grows, efficiency becomes a top constraint, limiting the ability to win more business in certain areas (49m32s).
• The US market has advantages like organic growth, brand recognition, and free benefits, allowing for more expensive lead acquisition methods, whereas international markets require more efficient approaches (50m8s).
• The company is working to find the right balance between growth and efficiency in international markets, where paid lead acquisition methods are more limited (50m21s).
• Early-stage companies often prioritize growth over efficiency, but established companies like Rippling have to operate within certain "guard rails" that can slow down growth, making it challenging to expand into new markets like Australia, which may seem small compared to the US market (50m44s).
• The HR software landscape in non-US markets, such as Canada, Europe, and APAC, is at least a decade behind the US, with fewer major public company payroll providers, making these markets ripe for disruption (51m22s).
• In most countries, there are only a few players in the HR software space, with one being an old, archaic system and the other being a modern startup with limitations in supporting various use cases, creating opportunities for Rippling to expand (51m51s).
• Rippling has a strong product-market fit and does well with multinational companies, but faces challenges in scaling pipeline generation and top-of-funnel growth due to inefficient spending (52m17s).
• Despite having a significant amount of cash, Rippling is disciplined in its finance function and avoids spending inefficiently on top-of-funnel growth, instead focusing on building word-of-mouth, local brand, and network effects within nations (53m3s).
• The company recognizes that the growth playbook is not the same in different markets and is cautious about spending inefficiently, as it may not work and could result in losing a significant amount of money (53m50s).
• Rippling's win rates and ACVs are good, but pipeline generation and top-of-funnel growth are scaling slower than desired, requiring a more efficient approach to growth (52m49s).
• Outbound sales have been the most scalable approach for growth, as demand generation methods can be expensive and may not be offset by referrals and word of mouth. (54m16s)
• To implement an effective outbound sales strategy, it is necessary to hire a large team of sales development representatives (SDRs), typically 20-50 people. (54m31s)
• Building an outbound sales team requires significant time and resources for ramping and training the new hires, which can delay the process of generating results. (54m35s)
• In contrast to outbound sales, paid advertising can produce quicker results, with the potential to spend a large budget, such as $1 million, to generate a high volume of demos. (54m40s)

Who Should Create the Playbook: Founders or Revenue Leaders (54m46s)

• Founders should not create the sales playbook, as they often have a strong product vision but may not think like the buyer or know how to transform their ideas into a consistent, repeatable sales playbook (54m46s).
• Founders are exceptional at articulating why someone should care about their product, but they may not be the best at creating a sales playbook, which requires a different set of skills (56m0s).
• Parker Conrad, the CEO of Rippling, is an example of a founder who is exceptional at go-to-market strategy, but he may not be the best person to create a sales playbook, as he thinks more like a product visionary than a buyer (55m22s).
• Founders should hire a salesperson from day one, as conventional wisdom suggests that hiring a sales team too early can be a mistake, but having a salesperson on board early can help create a sales playbook and drive revenue growth (57m0s).
• Hiring a salesperson early can help create a sales playbook that is tailored to the company's specific needs and can help drive revenue growth, rather than relying on the founder to create the playbook (57m5s).
• The speaker started working with Parker Conrad at his house when there were only four engineers, and they had no customers, CRM, or sales infrastructure in place, but they were able to build a successful sales team and create a sales playbook (57m31s).
• Founders often wait too long to hire a go-to-market leader, likely due to concerns about finding a good salesperson without significant traction, but it's beneficial to hire a sales leader early on, even with limited customers and revenue (58m12s).
• When hiring a sales leader, it's essential to look for someone with a high growth trajectory, often indicated by rapid promotions within the same company, ideally two or more times (58m51s).
• Rapid promotions within a high-growth company signal that the person is capable of adapting to new challenges and responsibilities, making them a strong candidate for a sales leadership role (59m38s).
• The ideal candidate may not have extensive experience, but rather a proven track record of growth and adaptability, such as being promoted from account executive to sales manager to director of sales within a short period (59m15s).
• It's challenging to attract top-tier sales leaders to early-stage companies, as they often prefer to join more established companies with higher revenue, typically above $60 million in annual recurring revenue (1h0m21s).
• Even successful entrepreneurs, like Parker from Rippling, may struggle to attract top talent to their early-stage companies, as seen in the example of Sam blonde declining an offer to join Rippling (1h0m45s).
• Mark Plank started at Zenefits as the 25th employee and grew up in the organization under Sam, eventually becoming a key executive, and when Parker was looking for someone to build an enterprise sales machine, he chose Plank due to his experience and success at Zenefits and Gong (1h0m52s).
• Normally, executives don't last at a company as it scales, with most falling out around the $10 million in annual recurring revenue (ARR) mark, but Plank has managed to scale with Rippling, which has done exceptionally well (1h1m32s).
• The main reason executives don't make it is that they can't hire people better than themselves or acknowledge the organic growth they've built, leading to a lack of recognition of gaps in their team's abilities (1h2m0s).
• As companies grow, they often promote internal managers to directors, but these homegrown leaders may not all be able to scale, and it's essential to recognize when they're hitting a breaking point and need to be layered with additional support (1h2m51s).
• To scale successfully, companies need to be able to hire people who are better than their current leaders and acknowledge the organic growth they've built, rather than convincing themselves that their current team can handle everything (1h3m7s).

The Biggest Signs When Someone Isn’t Scaling (1h3m24s)

• The biggest signs that someone isn't scaling often show themselves in two ways, with the first being that the individual starts leading from the back instead of the front, meaning they believe their job is to tell people what to do rather than showing them how to do it and leading the way (1h3m25s).
• This mindset shift often occurs when someone reaches a director or VP level and thinks they no longer have to be involved in the day-to-day tasks, resulting in them losing the respect and admiration of their team (1h4m2s).
• When this happens, the team starts to fall apart, even if it's a winning team, and the individual can't recover from losing the locker room, which can happen to someone who was previously amazing but lost their way due to this mindset shift (1h4m21s).

Quick-Fire (1h4m31s)

• The competitor most respected in the HTM space is likely Pelocity, a legacy competitor that does a good job of selling around their product gaps and is often seen in most deals (1h4m56s).
• When losing to a legacy payroll provider like ADP, it's often due to being outsold, despite having a better product, which suggests the competitor is doing something well on the go-to-market front (1h5m30s).
• The sales tactic that has not changed over the last five years is working hard and hustling, which has always been able to get ahead, but is now less common and more of an advantage than it once was (1h6m12s).
• The company currently requires employees to be in the office three days a week, but also has remote employees across the world, providing access to better talent (1h7m18s).
• Despite the benefits of remote work, there is a belief that the company has lost something in terms of company culture by not having everyone in the office, and if possible, would prefer to have everyone in the office (1h7m32s).
• To be a successful sales leader, one should work for a CEO who has high ambitions and expectations, making them feel deeply uncomfortable, as this will push them to achieve greatness and get more out of themselves than they would by trying to push themselves alone (1h7m46s).
• The best CEOs are not always nice or friendly, but rather demanding and intense, like top sports coaches, and working for someone like this can help a sales leader grow and achieve more (1h7m58s).
• A sales leader should not choose a company because it seems chill or easy, but rather because the CEO is demanding and will push them to go to market aggressively (1h8m44s).
• A company's sales strategy should be impressive and effective, such as Rippling's macro strategy of breaking up their sales organization into specialized teams, allowing reps to focus on specific products and compete more effectively in hyper-competitive vertical spaces (1h9m9s).
• Rippling's sales strategy involved carving off a product account executive model and building a culture of partnership in deals, allowing reps to work together and sell multiple products to new logos (1h9m54s).
• This strategy, although operationally complex, has allowed Rippling to compete and succeed in spaces like finance and global payroll (1h10m14s).
• A good revops team is essential in making this strategy work and ensuring its success (1h10m26s).