20 Sales Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process

Summary Notes


In this episode of "20 Sales with Harry Stebbings," Harry sits down with Maggie Hott, the dynamic Director of Sales at Webflow, to explore her journey through the sales world and her approach to scaling sales teams. Maggie shares insights from her time at Slack during its hypergrowth phase and her early role at Eventbrite, emphasizing the importance of nurturing cross-functional relationships and showing appreciation across the company to support sales success. She also discusses the strategic timing of adding outbound sales to a PLG model, the significance of building for scale, and the nuanced considerations in structuring sales compensation. Maggie's experience as an angel investor and advisor, as well as her personal life as a mother, adds depth to the conversation, highlighting her holistic view of sales leadership and team building.

Summary Notes

Hiring Ahead of Sales

  • Harry Stebings advises against hiring ahead of sales, particularly in the early stages of a business.
  • The rationale behind this advice is not provided in the transcript.

"I will rarely ever advise you to hire ahead of sales, especially early on. And here's why."

This quote signifies the importance of careful timing when expanding a sales team, suggesting that premature hiring can be a strategic misstep.

Introduction to the Episode

  • Harry Stebings introduces the monthly episode of "20 Sales" featuring sales leaders.
  • Maggie Hott, Director of Sales at Webflow, is the guest, known for her energy and charisma.
  • Maggie's background includes six years at Slack during hypergrowth and being the founding sales hire at Eventbrite.
  • She is also an investor and advisor to Cowboy Ventures, Scribble Ventures, and Coalition Partners.
  • The episode is supported by questions from Danny Herzberg at Sequoia and Kai Mack.

"And today I'm so excited to welcome an incredible force of energy and charisma in the form of Maggie Hott. Maggie is the director of sales at Webflow where she leads their sales dev account exec and solution engineering orgs."

This quote introduces Maggie Hott as an accomplished sales leader with a significant track record in tech companies.

Sales Planning and Engagement Tools

  • Pigment is a sales planning platform that helps with Salesforce capacity and quota management.
  • Sales Loft is a sales engagement platform used by companies like IBM, Shopify, and Stripe.
  • Chargebee is a subscription revenue and billing management platform utilized by Freshworks, Okta, and Envoy.

"Planning, Salesforce capacity and successful quota management can define the trajectory of your business. That's why you need Pigment."

This quote emphasizes the importance of strategic sales planning and the role of Pigment in facilitating this process.

Maggie Hott's Background and Journey into Sales

  • Maggie Hott had a nontraditional path into sales, influenced by her early exposure to diverse cultures and her parents' work in nonprofits.
  • She studied global studies and Spanish in university, where she was inspired by Kevin Hartz's talk on Eventbrite.
  • Maggie's proactive approach led her to become the second SDR and then the top-performing AE globally at Eventbrite.
  • Her proactive outreach and persistence landed her a role at Slack, where she contributed to its growth from $12 million to over $1 billion in ARR.
  • Maggie transitioned to Webflow after being recruited, and she now leads their entire sales team.

"I've had a very nontraditional path into sales. I don't think anyone really ever wakes up when they're eight or ten or 15 and says, I'm going to go be in sales."

This quote reflects on the unconventional journey many sales professionals take before finding their career in sales, as shared by Maggie.

Importance of Follow-Up in Sales

  • Maggie Hott emphasizes the importance of the follow-up in sales, a practice that many overlook.
  • Her consistent follow-up and relationship-building were key to her success at Slack and in her career.

"I think the wonderful thing with your career is you did what so few do, which is the importance of the follow-up, actually."

Harry Stebings highlights Maggie's exceptional follow-up skills, which are often neglected in sales.

Cross-Functional Relationships and Appreciation

  • Successful sales teams require support from cross-functional partners like finance, marketing, operations, and product engineering.
  • Sales leaders should spend time with cross-functional partners to educate them about the sales process.
  • Sales reps should engage in virtual coffee chats, participate in Slack channels, and approach colleagues with appreciation and partnership.

"Essentially, sales is very often on an island on their own. But the reality is no sales team will ever be successful without the support of their cross-functional partners."

Maggie Hott underlines the necessity for sales teams to have strong cross-functional relationships for overall success.

Building Outbound Sales and Preparing for Scale

  • Slack initially focused on inbound sales, which Maggie believes was a mistake.
  • It is crucial to build outbound sales early and prepare the sales organization for future growth.
  • Companies should invest in tools and systems that can scale with the business, avoiding the need for future replacements.

"It is so important to build outbound early and build sales early again."

Maggie advises on the strategic importance of establishing an outbound sales motion early in a company's growth.

Integrating PLG and Traditional Sales

  • Combining Product-Led Growth (PLG) and traditional sales is possible but challenging.
  • Companies should understand their market and customer profiles to determine the appropriate sales strategy.
  • Product differentiation is critical to prevent self-serve products from cannibalizing potential enterprise sales.

"You can, but I wouldn't fully recommend it."

Maggie Hott expresses caution when integrating PLG and traditional sales models, emphasizing the need for clear market understanding and product differentiation.

Product Differentiation in Enterprise Sales

  • Product differentiation for enterprise sales involves more than just security features.
  • Enterprises require the ability to negotiate legal terms, such as MSAs (Master Service Agreements) and DPAs (Data Processing Agreements).
  • Customer success and support are crucial, including 24/7 phone support and dedicated customer success managers.
  • Different roles and permissions are necessary to manage internal access control as a company scales.
  • Enterprise security features like DLP (Data Loss Prevention), eDiscovery, and MDM (Mobile Device Management) are often included in enterprise packages.

"So many different ways. Well, at first off, obviously legal. So the ability to negotiate your legal, your MSA, your DPA, something else that's very common for kind of those enterprise features is customer success."

This quote emphasizes the importance of legal negotiations and customer support as part of the product differentiation when selling to large enterprises.

The quote explains that legal negotiations and customer support are key components of product differentiation in enterprise sales, highlighting the necessity of these features to meet the specific needs of larger companies.

Timing for Enterprise Product Differentiation

  • Founders should consider enterprise product differentiation when they have a certain level of ARR (Annual Recurring Revenue) and a near-proven product-market fit.
  • Understanding the pain point being solved by the product is essential.
  • Founders should be able to sell outside of their immediate network ("the friendlies") to prove market demand.
  • The right time to build an enterprise product and sales team is after establishing a solid customer base and understanding of the market.

"You need to have some ARR. This needs to be essentially not actually a fully proven product market fit, but pretty close to it."

Harry Stebings is highlighting the necessity of having some level of revenue and a near-proven product-market fit before considering enterprise product differentiation.

The quote suggests that a certain revenue threshold and confidence in product-market fit are prerequisites for moving towards enterprise product differentiation.

Outbound Sales Strategy

  • Outbound sales should not be delayed; it's a critical part of the sales strategy from the beginning.
  • The main goal of cold outbound is to build brand awareness and educate potential customers about the product.
  • Personalization is key in outbound messaging, with a philosophy referred to as the "1080 ten" rule, which balances personalization with company messaging.
  • Resource allocation for outbound sales depends on company size and available funds, and strategies may vary based on these factors.

"The right time is now. Never, ever wait on outbound."

Harry Stebings advises that the right time to start outbound sales efforts is immediately, emphasizing the importance of not delaying this process.

The quote stresses the urgency of initiating outbound sales activities, indicating that it's a crucial step that should be taken early in a company's growth.

Blurring of Sales and Marketing

  • Sales and marketing are increasingly intertwined, especially with the rise of customer education as a key sales strategy.
  • Marketing aims for broader awareness, while sales outbound needs to be personalized and targeted.
  • The "1080 ten" rule of outbound prospecting involves personalization and company messaging to make the outreach feel individualized.

"They need each other. So marketing, think about that. Know the bigger, broader awareness be billboards or articles or whatnot."

Harry Stebings discusses the symbiotic relationship between sales and marketing, with marketing focused on broad awareness and sales on targeted outreach.

The quote explains the complementary roles of sales and marketing, with each playing a distinct but interconnected part in the overall strategy to engage and convert customers.

Resource Allocation for Outbound Sales

  • Resource allocation for outbound sales must be strategic, with a focus on identifying the Ideal Customer Profile (ICP) and targeting them effectively.
  • Companies may need to prioritize outreach based on their size and funding level.
  • The success of outbound efforts can be measured by responsiveness to self-serve sign-ups and the ability to close deals quickly after initial contact.

"It's going to be very dependent on your company size and how much money you have to put towards outbound, candidly."

Harry Stebings acknowledges that the allocation of resources for outbound sales is contingent on the size of the company and the budget available for sales efforts.

The quote recognizes that a company's approach to outbound sales will vary based on its financial resources and scale, implying that strategy must be tailored accordingly.

Testimonials and Discounts

  • Founders should use discounts strategically, primarily to control the close date of a deal.
  • Discounts can be tied to customer actions, such as agreeing to provide testimonials or case studies.
  • It's important to understand the reason behind a customer's request for payment terms or discounts.
  • Founders should focus on acquiring logos (customer brands) early on, even if it means offering discounts, to build credibility and attract more customers.

"If you don't have to discount, don't discount. I actually think discounts should be used very selectively."

Harry Stebings advises against unnecessary discounting, suggesting that discounts should be used strategically rather than routinely.

The quote advises caution with discounting, emphasizing that it should be used with purpose and as a tool for influencing deal timing rather than as a default sales tactic.

Monthly Payment Expectations in Software Sales

  • Clients often request monthly payments for software, which is generally dismissed as an unrealistic expectation.
  • The idea is that monthly payments are not the norm in software purchasing.

"People asking for monthly payments, which I usually just laugh at that. It's like no one pays monthly for any software, but people are going to ask for everything they can get."

This quote highlights the speaker's view on the rarity and impracticality of monthly payments in the software industry, reinforcing the norm of more traditional payment schedules.

Hiring the First Sales Team Member

  • Early-stage companies should avoid hiring a head of sales due to lack of clarity in the sales process and target market.
  • Heads of sales can be expensive and may demand additional support systems that are not yet necessary.
  • It's advised to hire someone experienced in building sales processes from the ground up, rather than a seasoned leader from a large, established company.
  • The ideal candidate is someone with AE (Account Executive) experience at a hyper-growth company or someone who has recently stepped into a frontline management role but is still close to the sales process.

"Yes, I will rarely ever advise you to hire ahead of sales, especially early on."

The quote emphasizes the speaker's advice against hiring a head of sales for a startup, suggesting that it's premature and could lead to unnecessary costs and complications.

Importance of Ground-Up Sales Experience

  • The most crucial factor in the first sales hire is their experience in building sales processes from scratch.
  • The ability to set up tooling, pitch decks, and understanding how to tell a story is more important than experience selling to a specific customer type or deal size.
  • Founders can teach product knowledge and customer personas but not the intrinsic qualities like hustle, grit, and drive.

"What's most important is that they have built from the ground up before or they have seen it very closely."

This quote underlines the significance of hiring someone with hands-on experience in establishing sales processes, as opposed to just having industry-specific sales experience.

Hiring Multiple Salespeople

  • Hiring in pairs or groups is recommended, not for competition, but for efficiency in training and team collaboration.
  • Group hiring fosters a supportive environment and can be more fun and productive, especially in early-stage companies dealing with high volumes of inquiries.

"Yeah, you should always hire in multiple sets of sellers, not for competition, but because it's actually not that much more work to teach a group of people than to teach one person."

The quote suggests that teaching multiple new hires simultaneously is more efficient than one-on-one training and encourages collaboration among the sales team.

Identifying Non-Obvious Traits in Sales Hires

  • The ability to deal with ambiguity and embrace chaos are critical traits for early-stage sales hires.
  • Candidates should be tested for their response to constant change and their ability to handle the lack of stability in a startup environment.
  • During interviews, candidates should provide examples of how they've managed sudden process changes and their role in implementing new processes.

"First. One is the ability to deal with ambiguity."

This quote identifies the capacity to handle uncertainty as a key trait for potential hires in a startup setting, implying that adaptability is crucial for success in a rapidly changing environment.

Structuring the Hiring Process

  • A thorough hiring process is essential to avoid costly hiring mistakes.
  • The process should include multiple stages, such as recruiter screening, hiring manager interviews, and team meetings.
  • Instead of product demos, candidates should be asked to pitch something they are passionate about to assess their presentation and teaching skills.
  • Mock discovery calls are used to evaluate a candidate's research skills, curiosity, coachability, and how they handle feedback.

"It's pretty lengthy. It's a recruiter phone screen, hiring manager phone screen, whole panel of what we call a chronological interview..."

This quote outlines a multi-stage hiring process designed to rigorously assess a candidate's fit for the sales role and the company culture.

Handling Feedback and Insecurity in Sales Candidates

  • How candidates handle feedback during the interview process is indicative of their potential performance and adaptability.
  • Even if candidates are insecure, their reaction to feedback is telling; defensiveness or excuses are red flags, while openness to improvement is valued.
  • The ability to apply a growth mindset to feedback is essential for a career in sales.

"I mean, should you be in sales?"

This rhetorical question challenges the suitability of a candidate for a sales role based on their reaction to feedback, emphasizing the importance of resilience and a positive attitude toward improvement.

Reflecting on Past Mistakes and Feedback

  • The speaker shares a personal anecdote about a significant mistake made early in their management career.
  • The lesson learned was the importance of going slow to go fast, taking the time to consider decisions carefully, even in a fast-paced environment.
  • The story illustrates the value of learning from mistakes and the impact of hasty decisions on a company.

"I had probably the biggest learning lesson that I will ever have."

The quote reflects on a past mistake as a crucial learning experience, underscoring the long-term benefits of such lessons for personal and professional growth.

Importance of Meticulous Planning

  • Recognizes the significance of comprehensive planning and attention to detail in large-scale projects or changes.
  • Emphasizes the long-term impacts of decisions and the importance of considering potential blind spots.
  • Highlights the direct effect on team members' careers and earnings, reinforcing the need for careful consideration and thoroughness.

"So again, just because you're hyperscale does not mean that you should be reckless." "That can actually have huge impacts on my org's careers and the money that they make."

The quotes underline the idea that rapid growth or scale does not justify hasty decision-making. The speaker reflects on the importance of thorough planning due to the significant consequences that decisions can have on an organization and its employees.

Evaluating Candidates Through Questions

  • Focuses on assessing accountability by asking candidates about deals they've lost.
  • Seeks to understand whether candidates blame external factors or take ownership of their actions.
  • Uses stack ranking questions to gauge self-awareness and the ability to learn from others.
  • Encourages candidates to reflect on past experiences and how they could have improved.

"The first thing I want to know from you tell me about a deal that you've lost." "What I'm looking for here, it's actually okay if you were at four, but what I want to know is, what is it that those top three people that beat you did differently than you?"

These quotes indicate that the speaker values accountability and self-awareness in candidates. They aim to understand how candidates perceive their past experiences, particularly failures, and whether they can identify factors that contributed to their performance relative to others.

Encouraging Self-Reflection and Preparation

  • Asks candidates about lessons they would teach their younger selves to assess introspection and growth.
  • Inquires about topics candidates hoped to discuss, revealing their interview preparation and ability to anticipate questions.
  • Uses this approach to allow candidates to showcase their achievements and preparedness.

"If you could go back in time ten years and coach yourself on something that you wish you knew now, what would it be?" "What is something that I didn't ask you that you were hoping I would ask you?"

The quotes prompt candidates to engage in self-reflection and consider their professional development over time. The speaker also uses these questions to evaluate how well candidates have prepared for the interview and their eagerness to share their successes.

Choosing Companies Over Roles

  • Advises candidates to prioritize selecting the right company over chasing titles.
  • Stresses the importance of joining a "rocket ship" company for long-term career growth and success.
  • Warns against being misled by titles at smaller companies that may not offer the same growth opportunities.

"Choose the company, not the role." "Choose that rocket ship and you will ride it far."

The speaker suggests that career advancement is more likely to occur by joining a successful company rather than pursuing prestigious titles in less promising environments. The analogy of a "rocket ship" implies that aligning with a thriving company propels one's career forward.

Understanding Compensation Packages

  • Highlights the common mistake of candidates focusing on on-target earnings (OTE) and equity without understanding the details.
  • Emphasizes the need to consider quota attainability and the actual value of equity in different companies.
  • Advises candidates to ask critical questions about the components of their compensation packages.

"We have had so many AES come to us and saying, I have this counteroffer from this other company for $50,000 more. Can you match that?" "Equity is obviously a very complicated thing, but very often folks don't realize equity."

These quotes reveal the complexities of compensation negotiations and the importance of being informed about the specifics of an offer. The speaker warns against making decisions based solely on the apparent value of an offer without understanding the underlying factors that affect its true worth.

Sales Tactics and Strategies

  • Curiosity, empathy, and personalization remain crucial in sales, despite changes in the industry.
  • The shift away from the necessity of in-person meetings, valuing efficiency and the quality of the product over traditional relationship-building methods.
  • The impact of tools like Clary on sales forecasting and time management, demonstrating the importance of addressing customer pain points.

"Curiosity, empathy, personalization." "You no longer need to be on site every single time you need to meet with the customer."

The quotes emphasize the enduring importance of personalized customer interactions and the evolution of sales tactics. The speaker notes that while face-to-face meetings were once standard, efficiency and respecting customers' time have become more valued.

Supporting Working Parents

  • Advocates for workplace support for working parents, including benefits, resources, and community building.
  • Highlights the negative impact of inadequate support, citing statistics on women leaving the workforce.
  • Suggests practical measures such as support groups and mental health resources to retain working parents.

"Support your working parent." "That is the single most important thing that you can do to support parents is really give them that place where they know where to go seek advice and help."

These quotes stress the importance of providing a supportive environment for working parents. The speaker believes that creating a sense of community and offering targeted resources can help address the challenges faced by working parents, particularly mothers.

Advice for Sales Leaders

  • Warns new sales leaders against the pitfall of "super repping" or taking over their team's deals.
  • Encourages leaders to focus on coaching rather than direct intervention to foster learning and independence.
  • Emphasizes understanding team members' motivations to tailor coaching and motivation strategies effectively.

"Do not super rep." "Understand the why and what motivates your teams."

The speaker advises new sales leaders to avoid the temptation to directly manage their team's deals. Instead, they should understand their team members' motivations and focus on coaching to drive performance and development.

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