Carlos Delatorre on Hiring Salespeople and Building a Repeatable Pipeline

Harness chief revenue officer Carlos Delatorre argues that sales can be learned and that every account executive should generate pipeline. In this January 2025 conversation with Harry Stebbings, he explains hiring, prospecting, training and account management, drawing on his experience at MongoDB, Navan and other companies.

Delatorre first saw the appeal of sales as a teenager selling suits on commission. He earned more in a weekend than he could through many hourly odd jobs. He says charisma can help, but curiosity and empathy matter, and most of the work can be learned.

He considers sales more science than art: practices that look mysterious can be broken into components and taught. Some people connect ideas unusually well, but others can learn and replicate many of the underlying skills.

When hiring, he starts with the job that needs to be done rather than assuming past success will repeat. A candidate’s experience should be examined against the skills and circumstances of the new role, including what they can learn and how long that will take.

For an early-stage company, he recommends that the CEO develop the initial message and sales plays personally. Hire individual contributors to work alongside the founder, refine the target personas and test the message; hire a sales leader after there is conviction that the approach can be repeated.

He generally prefers experience selling a comparable type and size of deal over domain knowledge, except when the domain requires especially deep expertise. His framework is to identify the person’s attributes, the skills needed and the gaps that training must close.

In enterprise software, he looks for success at a challenger company, experience sourcing pipeline, and familiarity with comparable deal complexity, account size, stakeholders and price. Some requirements are negotiable; too many gaps lengthen the ramp.

For a challenger, experience working without a dominant brand is close to non-negotiable for him. So is successful self-sourced pipeline generation. A move from smaller to larger deals can be more negotiable if the candidate has the intelligence and drive to learn.

Interviews and references form his initial judgment. Near the end of the process, once the hiring team has conviction, he asks candidates to prepare and present a challenge. He considers it unfair to require substantial unpaid preparation too early in the process.

Hiring teams can disagree because interviewers recognize their own strengths in candidates while overlooking other gaps. A process-focused interviewer and a highly charismatic interviewer may notice different things; the team needs to compare those perspectives.

He favors hiring at least two salespeople together, primarily so they can help each other rather than merely compete. At MongoDB, he says, analysis found that a lone rep in a city had roughly four times the attrition of colleagues with local peers. That is a company-specific observation, not a universal remote-work benchmark.

For a hub selling a product that needs technical support, he suggests at least two reps and a sales engineer. Sitting together makes small questions easier to answer and gives new hires more chances to learn from one another.

Pipeline generation is valuable beyond adding opportunities. When a deal is stuck with one division or a junior contact, a rep can use the same prospecting skills to reach another stakeholder or a more senior buyer.

He has seen teams that outsource prospecting become increasingly selective about leads, expecting marketing and SDRs to do most of the work before an account executive engages. Reps who generate their own meetings, he argues, better appreciate and convert leads from other sources.

His model makes the account executive responsible for the pipeline needed to meet quota; leads from marketing, partners and SDRs add to it. Stebbings points out the accountability benefit: a rep cannot simply blame poor leads for missing the number.

Delatorre suggests dedicating about one day a week to outbound calling and another 10–15% of time to preparation and follow-up, roughly a third overall. This is his operating rule of thumb, not a ratio proven optimal for every territory.

He hires people who have already done the difficult work of self-sourcing. He says the experience of repeated unanswered calls and the eventual satisfaction of creating an opportunity matters when deciding whether someone will persist.

He strongly disputes the claim that outbound calling is dead. In his experience, voice calls are especially effective, while email and social channels can build familiarity before someone picks up. His estimates reflect his sales context and are not a universal conversion rate.

He recalls a colleague pursuing a security executive through repeated emails, calls and contact with an assistant. The eventual meeting appeared effortless to the executive, but it followed many earlier touches. The example illustrates persistence and the work behind a seemingly simple introduction.

Delatorre estimates that fewer than 10% of salespeople are excellent at pipeline generation. He treats that as a demanding skill correlated with elite performance, not a measured statistic for the whole profession.

His quarterly planning starts with an enterprise rep selecting about 20 target accounts with a manager. Each week the rep chooses one or two focus accounts, declared on Thursday, and researches them before the next prospecting day.

The research can include executives’ public comments, filings, job postings and other signals about the company. The rep develops hypotheses about problems the product might address instead of approaching every account with the same generic message.

For two accounts he suggests identifying roughly 25 relevant contacts in each, with contact information, and doing deeper research on the ten highest-priority individuals. The goal is to prepare a useful conversation starter for each, not merely assemble a list.

Marketing supplies a Friday “pipeline generation passport”: concise material about releases, case studies and other news that reps can reuse. Managers review the declared accounts and add relevant context or introductions where they can.

On Monday morning, the manager reviews each rep’s preparation: are the contacts senior enough, too senior, or missing important stakeholders? Monday afternoon can be used for role-play and feedback on the message, persona or product.

Tuesday is the focused prospecting day. Reps call together, share what works, encourage one another after difficult calls and celebrate meetings booked. Delatorre sees that shared experience as a reason to favor hubs over isolated salespeople.

The week continues with follow-up and a Friday team wrap-up. He uses the latter to share successful meetings and opportunities from previous prospecting, reinforcing a practice that is difficult but important to the team.

Early in his career, prospecting often meant a single “power hour.” He found that an hour can pass without a conversation, leaving little learning or encouragement. A longer structured session gives more chance of feedback, though results still vary.

He warns against obsessing only over meetings booked. In his experience, around two to two-and-a-half meetings per week can be strong prospecting, but a rep can do good work in a week with none. The more important later measure is whether those meetings create qualified pipeline.

Stebbings tests the economics with a hypothetical: eight meetings a month, a 25% conversion rate and $100,000 annual contracts. Delatorre notes that self-sourced business is only one part of a territory: expansions, partners, SDRs and marketing may add opportunities. These figures are illustrative assumptions, not a promise of conversion or return.

He suggests that early teams may tolerate lower sales efficiency while finding product-market fit, whereas a scaling company might target a roughly five-to-one return or better. He thinks the outbound model can work for contracts around $50,000 and above, depending on cost and context; these are rules of thumb.

Asked about weak pipelines, he says the greater constraint in his experience is often enough ramped salespeople to pursue opportunities. He recommends breaking ramp into observable milestones instead of waiting a year for a final sales number.

Milestones might include training preparation, role-plays, early meetings, conversion and access to an economic buyer. Managers can identify where someone is going off course, diagnose the cause and coach them before a long enterprise sales cycle ends.

If a problem is fixable, help the rep get back on track; if not, the role or company may be a poor fit. Delatorre says he has sometimes parted ways during the first month, accepting responsibility for the hiring mistake rather than leaving both sides in limbo.

For training, his team describes a fully ramped salesperson, breaks the necessary knowledge and skills into competencies and selects the right format for each. The sequence should enable a new rep to land a healthy first customer as early as possible.

He describes a roughly nine-month learning journey with boot camp, intermediate and advanced sessions, plus recurring remote instruction with the same cohort. Early skills include prospecting and discovery; later training builds toward landing a new customer with the core product.

Reps can begin customer calls early using a messaging framework with value propositions, sample questions and proof points. Delatorre says they may be on the phone within days and begin generating pipeline before or during boot camp.

An early-stage startup cannot necessarily build that training infrastructure and may not yet know what to teach. The founder should sell alongside a small team, learn from both won and lost opportunities, and then create a first, lightweight version of training.

He favors the MEDDPICC qualification framework for deal reviews, whether early in a messy sales cycle or late when a forecast deal needs scrutiny. The real benefit comes when reps use the concepts with one another without waiting for a manager.

When morale drops, he recommends stopping and discussing what the team is experiencing. A good manager should notice concerns early, but if a team is already in a slump, determine whether the problem is belief in the approach, skills, training or something else.

Delatorre distinguishes industry-specific playbooks from industry-specific sales teams. He values shared knowledge about each sector’s needs so reps can be relevant quickly, even when the product is horizontal.

For horizontal products, he worries that vertical-only territories can produce unequal opportunities: a team may look exceptional because it owns a particularly attractive sector. He prefers a mix where practical, while accepting that highly different implementations can require specialization.

On SaaS churn and unused seats, he thinks much of the adjustment had already worked through the businesses he could observe. That is a limited, time-bound assessment. He believes salespeople should stay involved in customer outcomes rather than close a large deal and disappear.

Discounting rarely creates a considered enterprise purchase if no champion believes in the solution, he argues. Once a buyer has decided to proceed, price or a phased ramp can address genuine budget constraints. He distinguishes that from using a discount to manufacture demand.

When a forecast deal slips, he wants the team to learn from the pain. Ask what the sales team failed to do or should have done differently, then change future behavior. Deals will slip and be lost; the key is extracting a useful lesson.

For sales leaders considering a CEO role, he recommends diligence on the actual problems the company needs solved and an honest assessment of personal skills. A go-to-market background may fit a commercial problem but not necessarily a product problem.

He describes his own CEO experience: he expected mainly go-to-market issues but found a more fundamental need to refine product-market fit. He says the team improved sales execution, yet he lacked the tools to lead the product work effectively. He describes the experience as painful.

One hiring mistake was relying on a candidate’s senior relationships and past results at a large company. Delatorre recalls expensive lunches with contacts who were not the actual buyers, while the hire lacked the prospecting skills to reach the people who mattered.

He expects AI to automate research and preparation, increase sales productivity and improve onboarding and matching. These are predictions about how the role may evolve, not established outcomes for every sales team.

He thinks people overrate charisma and relationship-building relative to the work of selling. He also favors in-person teams for learning, morale and manager feedback, based on his experience; the interview does not provide a controlled comparison with remote work.

For existing accounts, he wants account managers to prospect into new divisions and care about customer outcomes. Trust earned by delivering value can give the incumbent team an opportunity to address a new need before a competitor displaces it.

In a mature territory, he suggests a rep might spend roughly a third of time on prospecting, 20–30% on existing customers and the rest pursuing deals. The mix changes with the territory: a greenfield rep and an account manager with two customers need different allocations.

He rejects the myth of a closer who can persuade an unwilling customer to buy through psychological tricks. A coerced purchase may later churn or be rescinded. His formulation is that buyers buy; salespeople create conditions through discovery, education and a solution to the customer’s problem.

Brand matters, he says, especially because an unknown challenger needs reps who can open doors without a familiar name. He recalls an early medical-equipment sale in which he brought a competitor’s machine to a demonstration and offered it free if the buyer preferred it; seeing the comparison helped him win the deal.

His advice to a new sales leader is to resist pressure to hire mediocre people quickly. He would also like to change the profession’s reputation for being manipulative or greedy, which he believes can deter capable candidates.

At Navan, the pandemic caused travel revenue to fall by about 90%, he recalls. Founder Ariel Cohen redirected engineering toward expense management, while the team moved upmarket to enterprises willing to improve travel programs before travel resumed.

Delatorre credits the combination of the new product and enterprise strategy with helping the business survive. At the time the decision was frightening because the duration of the shutdown was unknown; its success is his retrospective assessment.