20 Sales The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them How The Best Sales Reps Do Customer Discovery 2 Elements Sales Teams Are Always Responsible For Sam Taylor, VP Sales and Customer Success @ Loom

Summary Notes


In this episode of "20 Sales," host Harry Stebbings is joined by Sam Taylor, VP of Sales and Customer Success at Loom, to discuss the intricacies of building and scaling sales teams in tech companies. Taylor shares his journey from environmental consulting to leading sales at high-profile companies like Salesforce and Dropbox, emphasizing the importance of aligning sales strategies with customer goals and the future of work. He stresses the need for sales reps to be workflow therapists who listen deeply and adapt their approach to the culture and workflow of their clients. Taylor also touches on the challenges of integrating product-led and enterprise sales motions, the significance of cross-functional relationships, and the power of community in go-to-market strategies, as seen at companies like Notion. The conversation covers hiring sales talent, the value of cross-functional engagement, maintaining a customer-centric approach despite automation, and navigating the current macroeconomic environment.

Summary Notes

Introduction to "20 Sales" Podcast

  • "20 Sales" is a monthly sales show featuring interviews with leading sales leaders.
  • The show focuses on revealing sales tips, tactics, and strategies.
  • Hosted by Harry Stebbings.

This is 20 sales the monthly sales show where we interview the best sales leaders to reveal their tips, tactics and.

The quote introduces the podcast's theme and purpose, which revolves around sharing insights from top sales leaders.

Guest Introduction: Sam Taylor

  • Sam Taylor is the VP of sales and customer success at Loom.
  • Loom is a tool for hybrid and remote teams, allowing for screen and camera recordings.
  • Sam's role encompasses direct sales, customer success, self-serve sales development, and more.
  • His previous experience includes over four years at Salesforce post-acquisition of Quip, and over three years at Dropbox as a mid-market sales leader.

At Loom, Sam leads all things revenue.org, including direct sales, customer success, self serve sales development and more. And prior to Loom, Sam spent over four years at Salesforce following the acquisition.

The quote provides a brief professional background of the guest, Sam Taylor, highlighting his current and past roles in significant tech companies.

Sales Infrastructure Tools: Harmonic AI and Endgame

  • Harmonic AI offers lead generation and qualification tools for sales teams.
  • Endgame is creating the product-led sales category with a new product for identifying and targeting key accounts and users.

First, lead Gen, Brex, Ramp, vouch Carter and many others are using harmonics filters to define their ICP and build feeds of companies that are matching their criteria, whether it be newly formed, recently funded, key hires made, etc.

This quote explains the functionality and benefits of Harmonic AI's tools in identifying ideal customer profiles (ICPs) for businesses.

Sales Engagement Platform: Sales Loft

  • Sales Loft is a sales engagement platform that aids in prospecting, managing deals, and providing insights for sales teams.
  • Used by companies like IBM, Shopify, and Stripe.

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

The quote emphasizes the role of Sales Loft as a leading platform in enhancing sales team performance and revenue generation.

Sam Taylor's Entry into Tech and Sales

  • Sam Taylor's journey into tech and sales was not direct.
  • Held various jobs in different industries before starting in tech and sales at Salesforce in 2010.
  • Joined Dropbox as one of the first salespeople and then Quip, leading to a return to Salesforce.

Ultimately got my start on both the technology and sales side at Salesforce back in 2010, was fortunate enough to stumble my way into the Dropbox organization as one of their first five salespeople back in 2011.

The quote outlines Sam Taylor's career trajectory, highlighting his initial roles at Salesforce and Dropbox.

Key Takeaways from Salesforce and Dropbox

  • At Dropbox, the focus was on providing value beyond security in product-led sales.
  • The importance of aligning with customer goals and enabling efficient workforces.
  • At Quip, the emphasis was on workflow impact and value proposition.

I think the early learning for me, particularly as we were building the direct sales motion in tandem with the product lick side is security is not enough.

This quote reflects Sam's insight from Dropbox, where he learned the necessity of offering more value than just security in their product-led approach.

Product-Led Growth and Enterprise Sales

  • The decision to implement both product-led growth (PLG) and enterprise sales depends on the offering.
  • Loom started with PLG and later added a sales team as the product and market evolved.

So if I'm reversing back what I just said, it's think about who is going to be involved in being able to make a decision of is this applicable to me?

The quote discusses the strategic consideration of when to implement a sales team alongside a product-led approach, based on the decision-making process of potential buyers.

Product Marketing Challenge

  • Requires authentic curiosity and learning from users.
  • Sales teams need to package user experiences and business impacts effectively.
  • Salespeople should act as "workflow therapists," understanding individual motivations for using the product.

It requires that you have an authentic curiosity to learn from your users.

This quote highlights the importance of genuine interest in user experience as a part of effective product marketing in sales.

Discovering the Truth in Sales Questions

  • Open-ended questions help understand why users sign up and engage with the product.
  • Sales teams should use data to converse with heavily engaged users and understand their influence on others.

Well, I think there has to be a first principles of why were you compelled to go through and sign up and just see what they say?

Sam Taylor emphasizes the importance of open-ended questions to uncover the genuine reasons behind user engagement with a product.

Sales Playbook vs. Frameworks

  • Sam Taylor prefers the term "frameworks" over "playbook" due to its flexibility.
  • Frameworks should incorporate listening and adaptability.
  • Sales should involve storytelling and tailoring approaches to specific verticals or personas.

I don't love Playbook as a term because it sounds rigid.

The quote expresses Sam Taylor's preference for adaptable sales frameworks over rigid playbooks, emphasizing the need for listening and customizing sales approaches.

Role of Founders in Creating Sales Frameworks

  • Founders are inherently in sales when they raise capital and start a company.
  • Founders should create initial sales messages that are credible for the sales team to deliver.
  • Early customer-facing teams should have access to the founder's pitching process.

Well, I'd kind of call bullshit on the founder can't create it. Like if you raised money, you started a company and you're in sales, so you've already created that sales pitch.

Sam Taylor argues that founders are capable of creating effective sales frameworks, as they have already engaged in sales by starting a company and raising funds.

Onboarding Experience and Knowledge Transfer

  • Importance of allowing new customer-facing employees to understand the founder's "special sauce."
  • Founders should not underestimate their unique insights and practices.
  • The need for meticulous documentation of the founder's knowledge for new hires.

"Because there's so much that can be taken away from what is going to probably be perceived as table stakes, things that you've been saying for years that are actually going to be a huge unlock and highly applicable and inserted into the frameworks that that customer facing person is going to be able to reuse."

This quote emphasizes the value of a founder's accumulated knowledge and practices, highlighting how essential it is for new hires to have access to this information as it can significantly enhance their performance.

Documentation Strategies for Founders

  • Founders should consider creating scripts or recording their sales calls.
  • The goal is to provide a "treasure trove" of information for new hires.
  • The importance of identifying successful customer interactions for analysis.

"Should I create like word docs with the script that I use, the core. Value props that I say to the different people within orgs? Should I record my calls on certain sales loft or whatever we're using?"

This quote suggests practical methods for founders to document their sales processes and value propositions, which can serve as a resource for new sales hires.

Analyzing Successful Customer Interactions

  • Study customers who "got it from day one" to understand why they succeeded.
  • Look into the dynamics of the customer's role, the phase of their company, and key identifiers.
  • Aim to replicate successful onboarding experiences.

"Analyze those, don't take them for granted."

The quote stresses the importance of not overlooking the insights that can be gained from analyzing customers who quickly understood and benefited from the product.

Hiring Strategies for Early-Stage Startups

  • The decision between hiring junior reps or seasoned sales leaders depends on the startup's needs.
  • Early customer interactions may be more support or success-oriented than sales.
  • New hires should focus on earning revenue (ERR) and gathering customer insights.

"I really view that our team is on the hook for two things, err and insights."

This quote highlights the dual responsibilities of early sales hires in a startup, emphasizing the importance of revenue generation and customer insights.

Managing Product-Led Growth (PLG) and Enterprise Sales

  • The balance between product-led initiatives and enterprise sales requirements.
  • Product leads should drive the company, especially when entering the enterprise market.
  • The importance of aligning product, marketing, and sales around significant milestones.

"Do you have a conflict running a PLG in an enterprise motion in one?"

This quote addresses the potential challenges of running product-led growth strategies alongside enterprise sales efforts within the same company.

Inbound and Outbound Sales Strategies

  • Understanding that inbound and outbound are different motions requiring different approaches.
  • Outbound sales require a more opinionated stance from the organization.
  • Importance of setting incremental milestones for outbound sales success.

"It's a completely different motion for your organization."

This quote clarifies that inbound and outbound sales should be treated as distinct strategies, each with its specific set of practices and expectations.

Challenges in Building an Outbound Sales Team

  • Recognizing that outbound sales is a muscle that needs to be built over time.
  • Dealing with the initial lack of visible results and maintaining motivation.
  • Cherishing early signs of success, such as engagement and repeatability.

"Maintaining the perspective on how do we push our teams, how do we push the collective company to continue making the investment."

The quote speaks to the challenge of staying committed to building an outbound sales team despite the slow start and emphasizes the importance of perseverance.

Hiring Process for Sales Positions

  • Founders should identify what they want to achieve with new sales hires.
  • The hiring process should include different filters and structured interviews.
  • Focus on candidates' enthusiasm, curiosity, and structured learnings.

"I think as a founder I would be taking inventory of what is the reason why you need to hire sales capacity today."

This quote suggests that founders need to have a clear understanding of their goals and requirements before starting the hiring process for sales positions.

Initial Recruitment Philosophy

  • The recruitment process is a two-way street, assessing candidate fit and convincing them to take a risk on the company.
  • Early conviction of mutual benefit leads to cross-functional group involvement in hiring.
  • Integration of customer-facing teams with product, engineering, and design is crucial to avoid isolation.

"That is like, do you seem to be a fit and have the right filters that we are looking for in terms of your experience?"

This quote emphasizes the importance of mutual fit between the candidate's experience and the company's needs.

"I think I'm a big believer early days that what you absolutely don't want is for your customer facing teams, your sales team, whatever it is that you're hiring to be on an island in any way, shape or form."

This quote highlights the belief that customer-facing teams should not be isolated but integrated with other functions within the company.

Integrating Cross-Functional Teams in Hiring

  • Selection of hiring panel members based on credibility and cross-functional relationships.
  • Hiring panels should assess candidates' potential to build credibility and relationships across the company.

"I personally, when I'm putting together panels, look for who culturally has some of the most deep cross functional relationships and the highest level of credibility across those folks."

The quote underscores the strategy of choosing panel members who are deeply connected and credible across the company to participate in the hiring process.

The Importance of Building Relationships

  • Building relationships with different teams is crucial for career growth and understanding the company.
  • Candidates for customer-facing roles should have the ability to connect with other teams and align with the company's mission.

"The absolute best thing that you can do for your career is to sit at lunch every day with anyone other than the sales team, go and make relationships with the product organization, the engineers, the folks that are here that are building."

This quote from Armando Mann advises on the importance of building relationships across different functions within the company.

Case Studies in Hiring

  • Case studies are seen as overly structured and less useful for assessing real-world problem-solving.
  • Preference for working sessions that simulate real problems the company is facing.
  • Giving candidates a prompt related to actual challenges, like customer objections, to gauge their problem-solving approach.

"I don't like case studies because I think they're overly structured."

This quote explains the dislike for case studies due to their rigid structure, which may not reflect real-world scenarios.

Take-Home Assignments

  • Take-home assignments are used between the initial screen and the onsite panel.
  • Assignments allow candidates to demonstrate their approach to culture, leadership, and sales management.
  • Video submissions provide insights into candidates' communication styles.

"We do something called take homes, and it sits in between the initial hiring manager screen and the onsite panel we give folks."

The quote describes the use of take-home assignments as part of the hiring process to evaluate candidates' skills and thought processes.

Clarity in Hiring Goals

  • Founders must have clear goals for the role they are hiring for.
  • Avoid too broad or too narrow a focus in the hiring process.
  • Structure questions and cross-functional panel focus areas to avoid repetition and ensure a comprehensive evaluation.

"One, not having clarity on what they want early on, like what is the actual goal of this role, and having conversations early on."

This quote stresses the common mistake founders make by not having a clear understanding of the role's objectives from the onset.

Sales Compensation Advice

  • Variable compensation should be used judiciously, especially for early hires.
  • Early compensation models can include base salary with potential upside.
  • Compensation should be aligned with informed data and reasonable expectations.

"I think variable compensation is an excellent lever at the right time, and I don't think the right time is going to be your first couple of hires because you got no data."

This quote advises against using variable compensation too early in the hiring process due to the lack of performance data.

Onboarding Process

  • Onboarding should start with understanding the company's community, mission, and values.
  • Product knowledge and industry trends are crucial for new hires to become effective ambassadors.
  • Early onboarding includes cross-functional interactions and deep product training.

"Most important thing is you are hiring someone in its most simple form, in my opinion, to be an ambassador and extension of your product and your brand."

The quote emphasizes that new hires should be seen as ambassadors of the company's product and brand, necessitating a deep understanding of the company and its values.

Assessing Readiness Through Mock Exercises

  • Mock exercises and demonstrations are used to validate readiness to interact with customers.
  • Building a culture of coaching and openness to feedback is essential.
  • Feedback from peers and cross-functional teams is solicited during these exercises.

"Absolutely. There's something ceremonial about getting through the fire, so to speak, of validating your readiness to talk to customers in front of your peers and in front of a cross functional group."

This quote highlights the importance of mock exercises in assessing a new hire's ability to represent the company to customers.

Expectations for Delivering Value

  • Expectations for delivering value vary by segment and deal cycle.
  • Leading indicators, such as account multithreading and pilot engagement, are important for longer deal cycles.
  • The ramp schedule should align with realistic expectations for pipeline development and deal closure.

"Within the first 90 days, you should start to see deal flow realistically."

This quote sets a general expectation for new sales hires to begin contributing to the company's deal flow within the first few months.

Key Theme: Identifying Early Signs of a Poor Hire

  • Great hires show enthusiasm and ask high-quality questions across functions.
  • Lack of engagement and passive learning are red flags for new hires.
  • Building relationships and understanding the "why" behind tasks are indicators of a successful hire.

"Those that are coming in that are great hires are asking really high quality questions and they're not just asking them of their team, they're going on a freaking fact finding mission cross functionally, and they're building relationships to go and do it."

This quote emphasizes the importance of inquisitiveness and proactive engagement with various teams as characteristics of a strong new hire. It suggests that good hires go beyond their immediate roles to understand the broader workings of the company.

Key Theme: Cross-Functional Engagement in a Remote World

  • Leaders should facilitate cross-functional engagement in remote settings.
  • Providing a "listening tour" list and question prompts can help new hires initiate conversations.
  • Engaging with support teams can offer valuable insights due to their direct customer interactions.

"We literally give people a list of cross functional folks that should be on their we refer to as a listening tour. And we also give prompts of not for each person by function, but just what are the types of themes or types of questions that you should feel emboldened to ask that person?"

This quote describes a practical strategy for encouraging cross-functional communication in remote work environments. It suggests that structured guidance helps new hires to effectively engage with various departments.

Key Theme: Conducting Deal Reviews

  • Deal reviews are iterative and driven by segment leaders.
  • The cadence of deal reviews at Loom is biweekly.
  • Reviews serve as both deal analysis and post-mortems to learn from successes and failures.
  • Cross-functional attendance in deal reviews, including the product team, is encouraged.

"So I'd say iterative for us as we've scaled the team, just because we've moved from being there, being four sellers a year and a half ago, we can all just sit in the proverbial zoom room and break it down together to broader cross functional teams."

This quote explains how the process of deal reviews has evolved at Loom as the team has grown. It highlights the importance of adaptability and cross-functional collaboration in the review process.

Key Theme: Prioritization in Sales

  • Understanding why a deal wasn't a priority is crucial.
  • Building strong relationships allows for candid conversations and insights into customer priorities.
  • Not all reps will get the needed feedback, but strong relationships increase the chances.

"Ultimately, you are having to go through the process when you're doing that post mortem on why wasn't it a priority? And you could argue that that is ultimately what sales is, is how do you take something that is not a priority and find a path to making it one?"

The quote captures the essence of sales as the process of shifting a customer's priorities. It underscores the importance of post-mortem analysis to understand and address the reasons behind a deal's lack of urgency.

Key Theme: Reasons Why Enterprises Don't Buy

  • Current macroeconomic conditions lead to cautious spending.
  • Loom is in the early stages of establishing itself as an enterprise solution.
  • The challenge lies in educating the enterprise market about the category and demonstrating value.

"Well, I think broadly, we're in a macro environment where everyone is just looking at spend across the board."

The quote acknowledges the broader economic context affecting enterprise purchasing decisions. It suggests that external factors play a significant role in the sales process.

Key Theme: Sales Tactics Over the Last Five Years

  • Genuine curiosity and understanding of customer needs remain unchanged.
  • Authenticity and value-driven approaches are timeless in sales.

"The genuine and authentic curiosity in understanding your customers needs is the consistent like how does that play into your discovery? How does that play into your approach?"

This quote reaffirms the enduring importance of genuine curiosity about customer needs in sales. It implies that despite changes in tactics, the core principle of customer understanding remains vital.

Key Theme: Sales Tactics That Have Lost Effectiveness

  • Email automation has led to a saturation and exhaustion of email as a sales channel.
  • Finding alternative ways to cut through the noise is necessary.

"I think with all the automation that's taking place, particularly on the mostly email side, I think there's just an exhaustion around email today and trying to find ways to cut through that noise in different, more compelling ways."

The quote reflects on the decreased effectiveness of email due to overuse and automation. It suggests a need for innovative approaches to engage potential customers.

Key Theme: Founder Mistakes in Hiring Sales Teams

  • Founders often fail to integrate sales teams with the rest of the company.
  • Sales should be leveraged as a learning engine for the organization.

"What sales tactics have died of death? ... Not being intentional into the integration with the rest of the company?"

This question and subsequent explanation point out a common mistake founders make by not fully integrating sales with other company functions, thereby missing out on potential synergies and insights.

Key Theme: Advice for New Sales Leaders

  • Building cross-functional relationships is key for new sales leaders.
  • Understanding and translating customer feedback to the company is crucial.

"It's all about relationship building cross functionally, because if you're delivering feedback or if there's things that you have conviction that you've learned that you want to be doing from a go to market perspective, but it's falling on deaf ears or you don't have the credibility to deliver that in the right way, you have to go deep on those relationships."

The quote emphasizes the importance of relationship building for new sales leaders to effectively communicate and implement go-to-market strategies within the company.

Key Theme: Changing Perceptions of Sales

  • Aligning genuine curiosity with customer value is crucial.
  • There is a need to shift the perception of sales from transactional to value-driven.

"I think we're still fighting the potential misalignment between what I just said is the most important thing at the top of this rapid fire, which is like your genuine curiosity and customer understanding and value that you're driving for them and the way in which sales can be perceived particularly on the coin ops side of things, of just here for the paycheck."

This quote discusses the challenge of reconciling the perception of sales as a purely transactional role with the reality that genuine curiosity and customer understanding are at the heart of successful sales strategies.

Key Theme: Notable Sales Strategies

  • Notion's use of community to drive user base growth and ecosystem development is impressive.
  • Community involvement can be a powerful element in sales strategy.

"My wife Kate, who you've chatted with in the past, is over at notion. And I think that notion has done an amazing job of unlocking and unleashing the power of their community as a way to compound not only their growing user base, but the ecosystem that they're building."

The quote highlights Notion's strategy of leveraging community to enhance growth and create a robust ecosystem, which is seen as a model worth emulating.

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