Steve Goldberg on Selling to CFOs, Reviewing Deals and Building Customer Trust

Salesloft chief revenue officer Steve Goldberg tells Harry Stebbings that he sees a shift toward performance-driven sales management. He says finance leaders scrutinize budgets, but that does not mean they have stopped buying: vendors must show why their product solves an important problem.

Goldberg studied sports psychology and played catcher in college. Managing a team's momentum and encouraging a struggling pitcher made him interested in motivation. He later came to see sales as a combination of psychology and problem solving rather than the negative stereotype he once associated with the profession.

Goldberg recalls telling a prospective customer that he was there to sell something, but also to help solve its problem. For him, the best sales work helps customers succeed professionally. Stebbings asks how he learns enough about people to do that.

Goldberg looks for both business and personal motivations, asking what a professional and personal win would look like. He recommends conversations and preparation: learn about a person's background and interests, observe how they communicate, and connect that understanding to the problem being solved.

Asked how many prospect calls a new representative should make, Goldberg declines to prescribe a number. He favors a smaller number of well-prepared, high-quality conversations over activity for its own sake, with research into the person, the problem and the timing.

A person who likes the product is not necessarily the decision maker. Goldberg distinguishes large enterprises, where internal politics matter, from smaller businesses where buyers may be operators. He tries to understand how a contact will make the case internally and respond when the CFO or CEO challenges the purchase.

Goldberg warns against relying on someone who insists the seller speak only to them. In a large company, roles and influence change; a person's title alone does not establish how much authority they have. He recommends examining the organization's culture and the person's position within it.

He looks for a change agent who can move a decision through the company, observing how they communicate and whether colleagues follow their lead. A champion need not be the economic buyer: a revenue-operations director may drive a project while the CFO ultimately approves the expenditure.

If a champion leaves, Goldberg says a seller should not rely on that as a complete explanation for losing the deal. Multiple relationships reduce the risk, and trust may help a contact disclose a possible departure early. The aim is to surface bad news before it becomes an end-of-quarter surprise.

First-line managers should own deal reviews, while senior leaders design a consistent framework and questions. At the start of a quarter Goldberg wants teams to understand the problem, the unique value proposition, buyer agreement and gaps in qualification. A manager's role is to help untangle obstacles, not merely inspect a forecast.

By mid-quarter, he wants a mutually agreed plan with the buyer and regular tracking of the steps required to complete it. Goldberg says dishonest or overly optimistic reporting makes a review ineffective. He also reviews deals separately with managers and sellers to compare what each understands.

Goldberg recalls working for sales leader Dave Rudzinsky, whose detailed Friday forecast reviews required managers to know the status and next steps of every opportunity. Because he had to arrive prepared, Goldberg carried the same discipline into his own team. The purpose was to minimize surprises.

In late 2023, Goldberg sees the market moving away from a more nurturing environment toward a performance-driven one. He recalls a stricter culture earlier in his career but says leaders must still treat people respectfully and apply expectations consistently. Repeated surprises should also prompt questions about the manager's coaching.

To assess grit, Goldberg says Salesloft uses lengthy interviews that follow a candidate's life and career decisions. Interviewers ask why the person chose a school, changed roles or persisted through a challenge, looking for patterns rather than relying on a single anecdote.

Frequent job changes are a reason to ask for context, he says, and references can help validate claims. Goldberg also describes a practical exercise: candidates conduct a discovery conversation, then present the problem, business case and how they would help solve it.

Stebbings asks whether all budgets now go to CFOs and whether finance chiefs have stopped buying. Goldberg says purchases are getting CFO scrutiny, but buyers still spend on significant problems. He cites recent large deals and recalls major Salesforce sales during the 2008 financial crisis as examples from his experience.

Every renewal, Goldberg says, should be treated as a new deal. His own CFO asks what would happen if a product were removed. In a tighter environment, a seller has to show why the service matters, rather than assuming an existing subscription will continue.

Goldberg describes a management priority of getting better before getting bigger: train a smaller core team to solve customers' important problems and find people who can lead change. Stebbings challenges whether efficiency can persist as a company grows; Goldberg responds with an example of changing Salesloft's process.

Salesloft's commercial business had used a hunter-farmer model: a seller won a customer and later handed the account to an account manager. When customers stopped expanding and some reduced seats, managers stayed too close to their original contacts. Goldberg says the company shifted toward finding new use cases and relationships across each account.

As part of that change, account managers had to interview for redesigned roles, renewals moved to a customer-success renewal manager, and client account executives took responsibility for expansion. Goldberg presents this as his company's response to downgrades, not a universal organizational template.

He says customer-success staff should enter before a deal closes, so buyers understand how implementation will deliver the promised outcome. Salesloft also builds production environments around a use case to show prospective customers what working together would look like. Goldberg reports encouraging results but does not give a comparable win-rate figure.

Different businesses may need different customer-success structures, Goldberg says. In his workflow business, implementation spans processes and integrations. He worries that customer-success teams can become reactive support desks if they lose access to senior buyers and spend all their time answering administrative questions.

Goldberg does not think a CEO should personally act as the sales rep closing every large deal. A CEO should give the buyer confidence in the company's vision and connect with peer executives. Large purchases also require relationships among finance, technology, product and other teams on both sides.

A sales playbook should fit the segment and offer both strategy and practical steps within a consistent framework. Goldberg agrees that a startup founder should create the first version, including positioning, ideal customer, pricing and the initial selling approach.

Goldberg recalls founder Kyle Porter being able to persuade an individual through passion for Salesloft's product. As the company grew, it needed a repeatable process for persuading multiple stakeholders and selling a broader platform. He argues that scaling enterprise sales requires infrastructure that many product-focused founders have not yet built.

Goldberg regards revenue operations as exceptionally valuable because it connects data to decisions and uncovers blind spots. As a rough guideline, he suggests hiring a strong analyst around $5 million in revenue and building management capacity as the company grows. The numbers are his rules of thumb, not fixed thresholds.

One example of a revenue-operations insight was detecting downgrades in particular customer segments even when accounts were not cancelling outright. Salesloft used that data to change how its teams managed and expanded relationships. Goldberg says the value lies in seeing the trend early enough to act.

Buyers increasingly ask vendors to demonstrate outcomes, not simply usage, Goldberg says. Salesloft shifted its customer measures toward results such as pipeline and revenue, with leading indicators and health scores to identify accounts needing attention. Its teams follow up when those indicators change.

He describes examining specific customer workflows and integrations, then using regular executive business reviews to show leaders insights and recommendations. In a crowded market, he argues, a vendor must demonstrate how it delivers the promised outcome throughout the relationship, not merely list features before the sale.

Goldberg does not reject discounts outright. He cares about the whole contract, including the services and support needed for a customer to succeed, while procurement understandably focuses on unit price. He prefers negotiation in which both sides can support the resulting relationship rather than treating it as a winner-take-all contest.

Stebbings asks how to create urgency without damaging a relationship. Goldberg advocates agreeing on a mutual timeline early and having a candid conversation if the seller needs a decision by a particular date. He does not want a surprise demand at quarter-end that ignores the buyer's circumstances.

A large deal can feel lost and recovered several times. Goldberg calls sales a team sport: build relationships across the account and involve managers or colleagues when difficult conversations are needed. A strong relationship builder may need a teammate who is comfortable asking for a decision.

Goldberg expects AI to help salespeople prepare and have more informed conversations. He thinks some transactional or inbound work could eventually be automated, but says the five- or ten-year outcome is uncertain and warns against assuming every automated experience will be good.

The enduring sales principle, in his view, is solving business problems. He thinks relationship-building rituals such as golf and long lunches have become less central as people reassess their time. Creative deal-making can instead involve financial structure that gives both sides a stake in success.

Goldberg advises a new sales leader to learn each role deeply before seeking the next one. He says his own experience as an individual contributor helped him coach later, and warns that sellers and managers can rush into promotions before they are ready.

Having children changed how Goldberg organized his time and thought about other people. He compares the shift from selling to management with moving from catching the ball to coaching from the sideline: he now enjoys seeing colleagues learn, improve and earn promotions. He makes clear that this was his own experience, not a requirement for becoming a manager.

Goldberg points to his years at Salesforce as an example of a strong sales process and leadership culture. At a time when selling cloud software required earning trust, he recalls being transparent with customers about security and service. He credits a repeatable process aligned with the company's distinctive offering.