Sam Blond on Hiring Sales Teams and Making Outbound Work

Sam Blond tells Harry Stebbings that early sales hires need experience in a startup environment and that many young companies mistake a lack of sales opportunities for a conversion problem. He shares a practical approach to hiring, generating demand and making outbound outreach stand out.

Blond entered technology sales after graduating from the University of Missouri in 2007, helped by a brother who worked in the Bay Area. He joined EchoSign as a sales development representative when Jason Lemkin’s company was operating out of a Palo Alto garage.

As he began outperforming peers, he found success motivating. In hindsight, he says, he underestimated both how hard it is to build a successful startup and how much joining the right company can shape a career. He points to EchoSign, Zenefits and Brex in his own career.

For a larger startup, hiring trends, fundraising and revenue growth provide signals about its trajectory. At an earlier stage, Blond puts greater weight on the founders’ ambition and ability. He recalls being impressed by Parker Conrad at Zenefits; his confidence in Conrad’s later prospects is a personal prediction.

Stebbings asks whether sales at a fast-growing company is merely taking orders. Blond says the difficulty varies, but even strong businesses show large performance differences among representatives. He values sales partly because individual results can be measured relatively clearly.

When a founder is ready to hire, Blond recommends starting with two individual-contributor account executives. Once both are successful, he suggests hiring additional reps and searching for a sales leader in parallel, since finding the right leader can take months.

He generally waits until a sales leader is in place before hiring sales development representatives, because SDRs need close management. Before any of those hires, the founder should have closed a handful of paying customers outside friends and family and identified a process that appears repeatable.

The number of customers needed depends on the business: a transactional product may have many early customers, while two or three enterprise customers with large contracts might provide an initial signal. Blond believes founders are best placed to win the first customers and should not expect a salesperson to solve a failure to sell.

For the first two account executives, he prioritizes experience among the early sales hires at a startup and a record of strong performance. He also looks for familiarity with similar deal sizes and customer segments, since a transactional sale differs from a long enterprise cycle.

He thinks founders often overweight domain experience. An excellent early-stage salesperson can learn a new category, he argues, and restricting the search to a direct competitor may force a trade-off on more important qualities. His own career crossed electronic signatures, HR software and financial services.

Stebbings questions whether such candidates are too rare or expensive. Blond says they need not come from a famous company that became a multibillion-dollar success; strong reps can also emerge from less celebrated startups. His estimate that thousands exist is an illustration, not a census.

For sourcing, Blond recommends starting with the networks of founders, colleagues and investors rather than depending entirely on an external recruiter. He says Brex’s early sales hires came through personal networks, and each successful hire brought further potential referrals.

There may be no perfect candidate, so founders should decide which criteria are non-negotiable. One test Blond attributes to Jason Lemkin is whether the founder would buy from the candidate. He suggests asking a rep to pitch their current product, which they should know well, rather than the startup’s unfamiliar product.

For early compensation, he recommends entering the conversation with a market estimate based on the role and likely mature revenue productivity, then asking the candidate’s expectations. Cash, equity and deal size affect the answer; the ranges he gives are illustrative rather than a universal pay formula.

During onboarding, founders should share what they have learned about the sales process and give reps access to the information they need. An experienced early-stage hire should also bring ideas for generating and closing revenue in an ambiguous environment.

Blond recommends agreeing on 30-, 60- and 90-day milestones. He evaluates sales hires on revenue performance, effort and attitude. Some judgments are subjective, especially early on, and the milestones should reflect the actual company and sales cycle.

Stebbings challenges how quickly a rep can be evaluated when enterprise deals take months. Blond suggests watching leading indicators such as qualified opportunities and pipeline, not just closed revenue. He personally expects to see useful signals within roughly 30 days, while acknowledging that situations differ.

His hiring mistakes included ignoring concerns noticed during interviews because a candidate had made quota or the team needed to fill positions. A salesperson’s effect on colleagues and team culture matters alongside individual numbers, he says.

Blond often hears founders explain a missed quarter by pointing to a few deals that slipped. In his experience, many companies diagnose this as a conversion problem when their real constraint is too few opportunities entering the pipeline.

Stebbings pushes back: high-quality leads are difficult to find, and improving conversion may prevent wasting them. Blond replies that many sales teams have sparse customer-facing calendars and cling to weak deals because there is little else in the pipeline. His preference is to test whether opportunity creation is the bottleneck before concentrating resources in the middle of the funnel.

For a horizontal product, positioning can focus on a specific segment. Blond says Brex initially marketed itself as a corporate card for startups, even though competitor Divvy had used a similar cash-balance underwriting approach earlier. He credits the focused message with helping Brex gain traction before expanding.

He believes account executives should generate some of their own opportunities rather than waiting entirely for marketing or SDRs. At Brex, he says, AEs initially sourced more closed revenue than SDRs because they had better intuition about which accounts would convert and spend.

Brex responded by guiding SDRs toward accounts and personas with stronger outcomes and changing compensation from opportunity creation to revenue. Blond says SDR-sourced revenue then surpassed AE-sourced revenue, while the AEs continued sourcing their own deals. He uses the episode to argue for measuring quality, not just meeting volume.

Stebbings asks whether outbound has become obsolete in a world of content and communities. Blond still values it, but criticizes generic sequences sent by unknown representatives at unknown startups to a huge list of prospects.

He recommends targeting concentric circles, beginning with people close to the business: founders’ contacts, investors’ networks, employees’ previous colleagues and referrals from satisfied customers. The circle can expand as a company builds recognition and trust.

At Brex, he says, the sequence moved from personal and investor networks to Y Combinator companies and then to businesses near San Francisco billboards. A mature brand may eventually be able to reach strangers more effectively, but a startup cannot assume that recognition on day one.

The message should also stand out. Blond recalls sending founders champagne to congratulate them on recent fundraises, and suggests thoughtful physical outreach or handwritten notes where appropriate. These examples are tactics, not a substitute for understanding the buyer.

Stebbings worries that expensive sales and customer-success teams can overwhelm the economics of low-value contracts. Blond agrees acquisition spending should reflect customer value and segment; a tactic that works for a larger account may be too expensive to apply to a smaller one.

They discuss whether AI will flood inboxes and commoditize outbound. Blond sees automation as a way to streamline work and personalize messages, but believes human creativity still matters in devising an unconventional campaign. This is his view of the tools at the time, not a fixed limit on AI.

His method is to gather a small cross-functional group, ask each person for three different ideas for a channel, discuss them and test the strongest. He applies the exercise to outbound, events and paid advertising.

At a SaaStr event, he recalls Brex handing out breakfast burritos, using a magician at its booth, placing surrounding billboards and sponsoring branded hotel key cards. His point is to design several memorable touchpoints rather than relying only on a conventional booth.

For advertising, Brex used San Francisco billboards to reach a concentrated geographic audience. Blond also describes a Rippling campaign that offered gift cards to highly satisfied onboarding users who posted about their experience with a sponsored label. His account of cost and results is anecdotal.

Blond says Brex spent roughly $300,000 over three months on its launch billboard campaign. He recalls prospects mentioning the signs in outbound replies and believes the awareness helped customer acquisition and fundraising. He acknowledges that Brex was well funded and that many early startups could not afford the campaign.

A less successful experiment was a Brex restaurant and lounge in San Francisco. Blond says it was costly and distracting for a company with fewer than 100 employees. He cannot recall the exact expense and estimates it at hundreds of thousands to low millions of dollars, excluding opportunity cost.

He still thinks creative teams need to try unconventional ideas, even though not all will work. Stebbings agrees on experimentation while arguing that losses should be bounded.

On discounts, Blond favors a premium product and selective concessions late in a deal when they can accelerate a decision. He warns against discounting automatically: the concession should have a clear purpose and trade-off.

He believes generic mass cold emails are becoming less effective and expects more in-person customer meetings. At Brex, he says deals involving an in-person meeting closed at roughly three times the rate of those without one; that observation alone does not establish that the meeting caused the difference.

Blond prefers in-person teams for a new company, although he recognizes that an established remote business may find a reversal difficult. He criticizes sales cultures where representatives depend entirely on others for leads and argues for initiative and effort; these are his management preferences, not a measured comparison of working arrangements.

Stebbings says small acts of preparation and follow-up can help a young employee stand out. Blond agrees that attention to seemingly minor details can matter beyond sales. They close by thanking each other and looking forward to meeting again.