Matt Plank on Building Rippling’s Sales Organization and Scaling Outbound

Rippling chief revenue officer Matt Plank argues that building a sales organization requires careful segmentation, operational planning and collaboration with marketing. In this December 2024 conversation with Harry Stebbings, he discusses outbound prospecting, pricing, customer management and scaling leaders. His descriptions of Rippling and its competitors reflect his role at the company.

Plank says he enjoyed selling from childhood, from wrapping paper to appliances and knives. Competition motivated him, but he also learned that salespeople must be able to recover from rejection: even strong reps lose many opportunities.

He estimates that win rates vary substantially by segment and definition. A loss can mean a buyer chose a competitor, but at Rippling he says indecision or an unresponsive prospect is common. A rate measured only among deals with an explicit decision will therefore differ from one including stalled opportunities.

A lack of decision can mean the seller failed to demonstrate enough value, but priorities, budgets or personnel can also change. Plank advises treating people kindly after a rejection: a good relationship can create a later opportunity when timing improves.

He finds replacing an existing system easier than creating an entirely new budget category. When a buyer already uses a product, a sales team knows there is an existing need and can compete for it; a new category may require persuading the customer to change an established process.

Plank rejects the idea that outbound sales is dead. He says Rippling relied heavily on inbound demand early on and waited too long to build outbound, creating pressure when marketing could not grow form fills fast enough to support the next plan.

At the time, he reports roughly 1,000 outbound demos per month from the SDR organization, about half booked by phone. These are company-reported activity figures, not proof of close rates or a general benchmark. He credits Ashley Kelly with helping build the function.

He sees a close partnership with marketing as essential. Marketing identifies accounts and signals of interest, helps with messages and calling scripts, while SDRs execute. A new outbound team should create incremental pipeline, not simply add cost while replacing the same inbound meetings.

Plank says the culture should discourage sales and marketing from blaming each other or claiming all the credit. At Rippling, he says, marketing commits to a pipeline plan even though it does not report to him; the teams share responsibility for the outcome.

Planning begins with an ambitious company growth target and is broken down into many capacity plans by customer size, channel and product. The team estimates demos, hiring, quotas and staffing in each segment, then tests whether the combined plan can reach the target.

As the organization grows, he says the CRO’s work shifts from personally closing deals toward operational planning: deciding where capacity belongs and how many reps are needed for the opportunities in each segment.

Plank reports approximate win rates from Rippling’s stage-two opportunities of 50–60% at the smallest end, about 20% in mid-market and about 15% in enterprise. These are company-specific estimates from a broad entry stage, not comparable benchmarks without the same definitions.

At Rippling, stage two can include someone who attended a demo and agreed to follow-up without a tightly qualified budget or timeline. Stage three requires a second meeting and greater engagement, so a win rate measured from stage three will be higher. The denominator matters.

Rippling did not use outbound for its smallest customers, he says. Its mid-market segment covered roughly 50–250 employees, with an average deal of about $45,000 and an estimated sales cycle of 50–60 days. Those figures describe its product and customer base at the time, not a universal outbound threshold.

He says the product typically covers every employee and reports average pricing around $60–70 per employee per month across the customer base. That average and the $45,000 deal example are management estimates with different scopes and should not be treated as identical metrics.

As the product suite grew, sending every add-on sale back to the original new-customer rep became inefficient. A rep focused on high-velocity new deals might not give a much smaller expansion the attention it needed, so Rippling developed an account-management function.

Account managers own commercial relationships and renewals while also needing customers to succeed. Plank says Rippling also has technical account managers focused on adoption and retention, plus support. His preference for a commercially oriented account manager reflects this particular multi-product model.

Initially account managers were paid only on new revenue. After roughly nine to twelve months, Rippling changed the plan: he estimates about 70% was tied to new business and 30% to dollar retention. He says retention improved, but the interview does not establish a causal effect or provide a comparable churn series.

On discounting, Plank distinguishes list price from the net price a customer pays. He says price varies with company size, product mix, contract length and timing, but should follow a consistent policy that can be explained if customers compare quotes.

For a very early company, he prioritizes winning paying customers and validating that people will buy over maximizing the price of each deal. As the business matures, he advises gradually raising prices until it encounters meaningful buyer resistance.

He says unusually high win rates can indicate that pricing is too low or the company is pursuing too narrow a set of opportunities. That is a diagnostic hypothesis, not proof that every high win rate is bad; stage definitions and market conditions also matter.

Rippling incentivizes multi-year agreements, he says. His example of an additional commission depends on the base compensation rate and deal economics; the approximate percentages in the discussion are illustrations, not a compensation rule for every company.

Before offering a time-based discount, he says a rep should understand the buyer’s desired timeline and whether the buyer can actually move quickly. Offering a deadline too early can undermine leverage and create a poor customer experience.

He argues that a buyer who signs by a deadline often does so because the rep built trust and secured agreement during the evaluation, not simply because a discount might expire. The lesson is to understand the customer’s process rather than rely on artificial urgency.

Deal reviews should challenge optimism. Managers ask who the rep is speaking with, who makes the decision, what the timeline is and what evidence supports the forecast. Plank says Rippling generally holds weekly pipeline reviews between a manager and rep.

When a deal slips, he considers the rep’s historical forecasting pattern. A changed buyer, budget or priority can mean an evaluation must effectively restart, not simply wait a month. Some pushed deals ultimately disappear, so a forecast should reflect that risk.

A late legal review is frustrating to him when the rep forecast a firm close without first understanding the buyer’s contracting process. He recommends running legal and budget review in parallel with the evaluation when possible, rather than beginning them only after a verbal yes.

Plank says he had to learn not to react poorly when customers reject a deal. Thanking them, requesting feedback and preserving the relationship can lead to a future conversation. This is an approach to morale and relationships, not a guarantee that a lost deal will return.

A sales leader should own a missed plan instead of blaming the team or another function. He recalls advice from CEO Parker Conrad: knowing what to do personally is not enough; the leader’s job is to enable the team to execute.

He says Rippling’s sales reps did not have individual prospecting targets at the time; outbound SDRs owned that quota. Although many sales leaders favor rep-sourced pipeline, Plank prefers a specialized SDR funnel for as long as it works efficiently. This is his operating choice, not a universal rule.

He describes measuring the SDR funnel from accounts and dials through connection and demo rates, then finding and repairing the weak stage. He believes a structured SDR organization can execute that work more consistently than sales reps without comparable focus and management.

Plank regrets holding on to scripts, decks and pitch ownership for too long as the company expanded into many segments. He eventually hired experienced vice presidents and delegated those decisions. He wants leaders closest to the work to challenge outdated materials, even if he authored them.

Asked for the revenue split among SMB, mid-market and enterprise, he says the many direct, channel and product segments make a simple breakdown difficult. He describes the upmarket business as growing particularly quickly; he does not provide a precise revenue split.

He says international growth was slower than he wanted, even though he believed product-market fit and win rates were strong. Teams in Dublin and Sydney were adapting the approach to local markets. These are management assessments and plans from the interview.

Entering a new country is more expensive when the company lacks local brand, referrals and word of mouth. Rippling’s efficiency constraints limited how much it would spend to generate top-of-funnel demand before it knew which local playbook worked.

Plank sees opportunities in non-US HR software and says Rippling can serve multinational companies. His characterization of local competitors and product-market fit is the view of a competing executive, not an independent ranking of those markets.

He says outbound was the most scalable international channel at that stage, but hiring and training SDRs takes time. Stebbings challenges whether spending less efficiently at first could build a brand and improve economics later; Plank acknowledges that approach but worries about committing capital before learning what works.

Plank believes founders should hire go-to-market leadership earlier than conventional advice often suggests, potentially after some customers have paid. A strong partner can translate a founder’s product vision into a repeatable sales playbook and inform product sequencing.

He says Conrad is deeply involved in product direction and challenges the go-to-market team, but does not write every sales script. Plank values constructive disagreement in which the sales leader can defend an approach and persuade the founder.

For an early sales leader, Plank looks for steep growth in responsibility, such as repeated promotions at a high-growth company. He uses that as a signal that someone has handled new problems, although promotions alone do not prove future performance.

He agrees that a proven senior executive may not want to return to the earliest startup stage. A founder may find a promising leader one level below an established executive, as Plank says happened when Conrad recruited him from the Zenefits network.

Asked how he has scaled with Rippling, Plank credits the product, marketing and many other contributors. He believes leaders stall when they cannot hire people stronger than themselves or recognize that some internally promoted managers need new support.

One warning sign, he says, is a leader who stops demonstrating and helping with the work and begins only directing from a distance. In his experience, losing the team’s trust can undermine even a previously successful manager.

In quick fire, he respects Paylocity’s go-to-market execution while expressing a strong preference for Rippling’s product over legacy competitors. This is a competitor’s assessment, not an independent product comparison.

He values focused effort and misses the shared energy of an office. He says office-based employees at Rippling were expected in three days a week, while the company also employed remote staff; his preference for more in-person work is personal.

He advises a new sales leader to work for a CEO whose ambition and expectations stretch them. He frames this as a way to grow, although his preferred intensity is not a universal prescription for every workplace.

Plank highlights Rippling’s shift from generalist reps selling a large product suite to specialized product account executives. A core HR rep can work with finance or global payroll specialists, reducing the knowledge burden on one person while adding operational coordination.

He says that specialization helped the company compete in focused categories, while revenue operations managed the added complexity. His assessment of the strategy’s success is an internal view, not a controlled comparison.