Kevin Egan on Building Enterprise Sales Teams

Kevin Egan tells Harry Stebbings that he began at Oracle in the mid-1990s in data-center technical support before moving into sales engineering. The role gave him a foundation in both technology and selling. At the time of the interview he led global enterprise sales at Atlassian.

At Salesforce, Egan saw an early form of product-led growth: prospective customers could try the service free for 30 days while sellers helped configure it around business problems. He credits this combination of product access and customer assistance with strong conversion, a retrospective account rather than a published measurement.

Dropbox taught him the challenge of combining a product end users love with security and operational controls large enterprises can trust. He says Slack benefited from seeing that transition elsewhere and aimed early to serve large teams while retaining an engaging user experience. His assessments reflect his experience at those companies.

Egan prefers the term sales motion to playbook. A motion identifies the buyer, user, industry and business problem, then explains how the product uniquely creates value. He cautions against reducing a sale to a fixed sequence or a list of features.

Founders provide the inspiration and high-level explanation of how the product solves a problem; a sales leader’s job is to draw that out and make the approach repeatable in writing. Egan sees product-led and enterprise selling as compatible but hard to develop simultaneously because enterprise controls can take years.

He favors building end-user love first and adding enterprise capabilities as demand emerges. At Slack, he says, usage spread inside some companies until procurement and legal wanted formal terms and a strategic relationship. Tens of thousands of users within a company are examples from his account, not a threshold every business must reach.

Enterprise customers may require reliability commitments, data residency, access controls, encryption and data-loss prevention. Requirements continue to evolve, so Egan says enterprise readiness is an ongoing partnership rather than a short checklist. His mention of GDPR reflects the 2023 discussion, not legal advice.

Early sellers need to feed customer insight back to product: why users adopted the service, what problem it solves and how value might be measured. Once the motion becomes repeatable, he says, the organization can add more specialized roles such as sales development, account executives and sales engineers.

To assess whether a sales team adds value to a product-led business, Egan suggests comparing customers handled through online channels with a cohort supported by representatives. Activity and opportunity data can help measure the difference. A useful test still needs comparable groups and an interpretation appropriate to the business.

If the company can afford it, Egan favors hiring two or three representatives together. Comparing their progress can reveal both whether the motion works and which people execute it well. He notes that the companies he joined already had small teams, so this is his recommendation rather than a controlled experiment.

Hiring strong sellers requires a disciplined, multistep process, Egan says. He describes candidates meeting several people and presenting a mock customer scenario before receiving an offer. The exercise reveals whether they can understand a business problem, articulate a differentiated solution and handle objections in a room.

A mock exercise can use a fictitious company and the hiring company’s product, as he describes at Salesforce, or let a candidate pitch a familiar product, as at Slack. Stebbings worries the familiar product gives an advantage. Egan says interviewers can compensate by raising the difficulty of questions and objections.

He looks for consistency between interviews and the presentation. A candidate who interviews well can still struggle when challenged before an audience. He treats unexplained inconsistency as a signal to investigate, rather than assuming an impressive interview predicts field performance.

The type of seller changes with the company’s stage more than with a simple product-led versus enterprise label, he argues. Early representatives need breadth and enjoyment of building; later, specialists may focus more tightly on accounts and quota. He is more concerned about a purely compensation-driven approach in the early stage.

Egan cautions against hiring solely for a famous company name. A startup’s first sales leader may need to write messaging, close customers and communicate customer feedback to product without the support functions a large employer provided. He calls the ability and willingness to cover that range more informative than a logo.

Compensation must first be fair and informed by market data, he says. Once that condition is met, he looks for candidates who are excited about the company’s longer journey and their own development, not just a near-term package. That is his hiring preference; a candidate’s attention to pay alone does not establish motivation.

Trust with a new hire begins with clear expectations and more direct guidance. As the employee becomes competent, Egan tries to move toward a partnership and invite their ideas. He believes the manager’s role should be visibly broader than the employee’s, while still being attentive to the employee’s concerns.

Managers must be willing to explain plainly when expectations are not met. Egan treats direct feedback as one part of a working relationship, not a continuous stream of correction. He warns against feedback that is overly frequent, personal or diminishing and prefers feedback tied to the team’s priorities.

In the more uncertain 2023 buying environment, Egan says forecasting requires clarity about the customer’s business problem, expected return and reason to spend. He welcomes CFO involvement as a sign that an opportunity may be strategic, while emphasizing that sellers must communicate the financial case.

Pushing a deal through solely to meet a quarterly target can hurt a customer relationship or brand, even if it sometimes works. Egan says a healthy pipeline gives sellers alternatives when a deal slips. Early companies may need executive help to convey urgency in a way that still works for the customer.

Egan says Atlassian did not discount in his role at the time, instead using programmatic terms intended to be transparent and fair. At previous employers, discounting could work for both sides. This describes company practice in the interview, not a claim that every customer or future policy is identical.

Where discounting is used, he recommends a matrix set by the CFO, who understands margins and volume. A representative, manager and sales leader can have progressively different authority, with exceptions escalated. He says procurement teams may press startups harder and look for conviction in the value being offered.

Deal reviews happen at different frequencies across an organization. Egan spends two to three hours a week on them and favors a framework such as MEDDIC or MEDDPICC to examine stakeholders, business value and the path to close. The strongest managers, he says, focus on why a deal might fail, not only why it might succeed.

When a deal slips, he distinguishes a committed deal that missed the quarter from an opportunity the team merely hoped to pull forward. For a committed miss, he recommends a full review of whether the issue lies in pricing, product or sales execution. The distinction makes the response more useful than treating every delay alike.

In the quick-fire round, Egan says clear written communication about the customer’s problem and a plan to solve it remains valuable. Withholding technical information to force contact with a salesperson, by contrast, has become less effective as buyers expect transparency.

His advice to a new sales leader is to resist assuming the previous company’s pattern fits the next one. Spend time with peers, especially engineering leaders, to understand their view of the product and the problems it solves. Each environment has its own constraints.

Egan hopes AI can help sellers identify the best next step and bring customers stronger ideas, a future aspiration rather than a measured outcome. At Atlassian, he says a current challenge is giving customers an informed view of how tools such as Jira can help them ship better products.

Asked whom he admires, Egan cites Snowflake from a distance for apparent alignment and customer focus, while saying he has not bought its technology or worked there. Stebbings and Egan close the conversation with thanks.