Lauren Schwartz on Hiring Salespeople and Building an Enterprise Sales Team

Lauren Schwartz traces her interest in sales to selling cookies as a Brownie, where she enjoyed competition and finding ways to encourage repeat purchases. She later spent six years in sales at Google and attended Stanford business school before joining Segment and then Fivetran.

At business school she initially tried to distance herself from the label “salesperson,” because of its negative associations. She and Harry Stebbings describe a different ideal: helping a buyer understand a problem and find the right solution rather than simply persuading them to buy.

At Google, Schwartz says, she learned to cultivate curiosity about what is possible. A salesperson may need to ask uncomfortable questions about a customer’s current problems, but also has a responsibility to help the customer work toward a better situation.

She advises starting with open-ended questions: ask the buyer to describe the current state, its consequences and what a better future would enable. Then connect that future to business outcomes such as revenue, cost savings, risk reduction or faster time to market, instead of stopping at a technical feature.

Stebbings asks whether outbound sales still works. Schwartz says outreach is stronger when it is relevant and meets customers where they are. At Fivetran, she describes co-selling with partners including Snowflake, Databricks, Google Cloud and AWS, whose products connect to the data infrastructure Fivetran serves.

The host points out that an early startup may not have partnerships with such large companies. Schwartz recommends using the connections available, including investors and founder communities, to obtain warm introductions and build relationships early. Her examples reflect her position as a Fivetran sales executive and the company's commercial interests.

Salespeople at a startup both tell the product's story and collect information that can improve it. Schwartz recommends recording customer feedback in a CRM and sharing it through deal reviews, post-mortems and conversations across sales, product and other functions.

She thinks “playbook” can sound too prescriptive for a very early company. The founder is often the first seller, and initial sales hires need repeated customer conversations to learn the market, test the narrative and feed information back to product before a repeatable playbook is clear.

Schwartz recalls joining Segment as a small-business account executive after selling at Google. Shorter, higher-volume sales cycles gave her many opportunities to learn a new product, buyer and technical subject. That repetition helped her understand what worked and accelerate her ramp.

Asked whether startups must choose product-led growth or enterprise sales, she says some can succeed with a sales-led motion alone but founders may also wait too long to add sales. In her view, a small initial product-led foothold in a large enterprise can be complemented by a top-down team that expands adoption.

In a complex enterprise sale, she considers multi-threading critical: identify the customer’s champion, competing advocates, the case for doing nothing and the economic buyer. Rather than rely on one person's account, she tests and revises her understanding with several stakeholders.

That research lets a seller bring the buyer a picture of what their own team says about its needs and obstacles. Schwartz frames the work as helping the customer articulate and solve a business problem, not just delivering a pitch.

Stebbings asks what to say when a deal slips because it was not urgent. Schwartz asks who at the customer has confirmed the problem, why it matters and when it must be solved. Her team's three questions are why do anything, why now and why with Fivetran; without an answer to timing, she says, a supposed near-term deal may never have been ready.

The host asks whether discounts or personal relationships can create urgency. Schwartz prefers a mutual action plan built backward from the customer’s desired outcome. If a result is needed by the end of a quarter, implementation, approvals and professional services may require the purchase decision months earlier.

For a startup's first sales hire, she favors someone willing to explore the market, ask difficult questions and operate in ambiguity over a leader whose main experience is scaling an established organization. The hire must also follow enough process to compare experiments and learn from them.

Stebbings asks whether founders should hire two salespeople and pit them against each other. Schwartz supports multiple hires for a different reason: comparing results helps distinguish a problem with one seller from a problem with the product, message or market. It need not become a contest between colleagues.

In interviews, she warns against relying on polished stories or hypothetical 90-day plans. She asks candidates about previous quota attainment, the people involved in specific deals and what the candidate actually contributed. Concrete detail helps distinguish repeatable performance from a good presentation.

One favorite technique is to ask for the deal a candidate is most proud of, then discuss the second one instead. The change can move beyond a rehearsed story and show how the person thinks and adapts during a live conversation.

Stebbings raises attribution: a salesperson attached to a rapidly growing customer can look exceptional even if the sale required little work. Schwartz says to examine the employer's stage, the customer’s circumstances and each participant's role before attributing the outcome to one person.

She remembers initially being rejected by Segment because interviewers assumed her Google background meant she would not be scrappy. She responded with examples, and the concern was resolved. She thinks the interviewers were right to test the issue, even though their first conclusion about her was wrong.

She also asks about a lost deal to see whether a candidate recognizes their own contribution, takes accountability and explains what they learned. External factors can matter, but she looks for an ability to identify what the seller could do differently next time.

To understand the experience of buying from a candidate, she asks what a customer would say about working with them, who at that customer could speak to it and whether she may contact that person. This adds a customer reference to the candidate's own account.

Stebbings asks whether a sales interview should include a pitch or case study. Schwartz has used both a candidate's own product and the hiring company's product, but sees pitfalls: interviewers may not know the buyer's context, or may focus on stumping a candidate rather than evaluating useful skills.

Her alternative is an unprepared role-play based on a real situation, such as a deal in procurement. She wants to see whether the candidate listens, adapts and returns the discussion to the business outcome the customer seeks.

Her own hiring mistake was assuming a smooth presentation meant a candidate had the enterprise experience she needed. Different companies used different segment labels, and she had not investigated the actual deals deeply enough. The experience reinforced the need to examine specific contributions and deal context.

For onboarding the first sales reps, Schwartz emphasizes exposure to real customers: recorded calls, joining the founder or manager, and lower-risk opportunities to practice. Enterprise sales cycles can be long and individual opportunities consequential, so practice and context matter.

She also wants new hires to learn what has and has not worked through recorded calls, win and loss reviews and documented lessons. At Fivetran she describes a structured 90-day onboarding plan, with the pace of customer-facing work depending on the individual's readiness and the business context.

Because a major enterprise sale can take six to nine months, Stebbings asks how to assess a new rep before revenue arrives. Schwartz looks for leading indicators: whether calls advance, follow-ups are clear, trials are justified and the economic buyer is aligned before the company commits more resources.

She says the first 30 days can reveal signs of organization, curiosity and learning: how a person approaches the product, works across functions and seeks advice from strong colleagues. These are her early signals, not a guarantee of eventual sales performance.

Schwartz recommends frequent deal reviews, potentially weekly, without necessarily revisiting the same opportunity every time. The account executive should bring relevant cross-functional colleagues, such as a sales engineer or partner, so the team can identify gaps and decide what to do next.

At company-wide meetings, she values broader stories about a win, the lessons learned and what the team would change. Celebrating a customer logo alone does not transfer much knowledge to the rest of the company.

A painful loss can reveal a qualification error: the team invested resources in a customer problem its product was not intended to solve. Schwartz says that is disappointing but coachable. Another common competitor is the customer’s decision to do nothing.

If a buyer chooses not to change, she asks whether the team understood the pain and connected its product to a sufficiently important business problem. A project wanted by one practitioner can be deprioritized; the team needs to understand the wider enterprise's actual goals.

Schwartz identifies direct communication and transparency as strengths she tries to bring to leadership. She wants people to feel safe acknowledging mistakes and sharing what they learned, and models that by describing her own errors and taking responsibility.

She recalls being told that her rapid-fire questions during a deal review frightened a seller who did not understand her agenda. She learned to explain why she is asking and which risk she is trying to avoid, so the discussion feels like coaching rather than interrogation.

Stebbings objects that explaining the purpose of questions can allow someone to tailor an answer. Schwartz distinguishes an interview, where not leading a candidate can be useful, from ongoing management, where transparency and modeled accountability can help a team feel safe. Their disagreement concerns different settings.

In the quick-fire round, she avoids naming a single customer deal and says she is proudest of recruiting sales leaders and helping them achieve their own career goals. She says curiosity and rigorous qualification remain valuable, while she believes pricing disconnected from customer value is becoming less effective.

She wants more diversity in sales leadership and recommends building communities and candidate pipelines, promoting from within and making leadership paths visible to people from underrepresented groups. The automatically generated captions omit a brief answer around 46 minutes, so that response cannot be reconstructed reliably.

At Fivetran, she says her hardest challenge is keeping the team focused when leaders ask sellers to win new customers, expand accounts, retain them and increase consumption simultaneously. An overly complicated list of objectives can also make compensation difficult to understand.

Her principle for compensation is alignment with desired business outcomes. A short portion of the automatically generated captions is missing around 48:04–48:22, so her full response to the host's follow-up is unavailable. The remaining captions describe her preference for aligning incentives with product adoption and consumption, not only initial bookings.

Asked whether customer success should share incentives for expansion, she says it depends on the organization. In Fivetran's enterprise model, the account executive remains involved throughout the customer’s lifecycle rather than handing the account away after the initial contract.

She admires sales teams that build categories where no budget has already been allocated. In her view, those sellers must connect the product to a business outcome and earn a customer’s attention without relying on an established purchasing category.