Rippling on Leading Leaders

How Parker Leads Rippling

Rippling is 9 years old, has scaled to over 3,500 employees, and serves tens of thousands of customers globally. Today, Rippling generates over $100M in revenue and operates across four key workforce functions: (1) a modern HR platform to handle payroll, benefits, compliance, and onboarding, (2) IT tooling for device management and identity access control, (3) financial operations software, and (4) global infrastructure to support international hiring.

Example: Rippling’s Senior Reporting Structure

• Parker currently has five direct reports: 
  
  • CRO 
  • COO – spends 95% of his time acting as Head of Product
  • CTO 
  • CFO
  • CMO – currently reporting to the CRO 
• Not every senior hire should report directly to the CEO – Parker adjusts reporting lines based on leadership maturity, available managerial bandwidth, and the level of support each role requires. 
  
  • Parker doesn’t see reporting to the CEO as a promotion
  • He decided to have their new CMO report to their CRO, even though their former CMO previously reported to the CEO. For younger executive hires that may need coaching to grow into their roles, reporting to a senior leader with the bandwidth to guide them may be a better fit.  
• Several key leaders technically report to the COO but operate semi-independently:
  
  • Head of Customer Support & Success → reports to COO, but runs independently
  • Head of Corp Dev & BD → reports to COO
  • Head of Ops → reports to COO, but functions like a COO in-training

Great HR Execs are Hard to Find 

• Parker believes HR execs are often extremely weak and ineffective
• Rippling decided against having an independent executive to run HR – they instead opted for finding a capable generalist to run an HR business partnering function instead.
• HR often evolves into a ‘union representative’ for employees. Instead, the job scope for HR at Rippling focuses only on strengthening their performance culture. 
  
  • At Rippling specifically, Parker is the sole account admin of the company’s Rippling instance, keeping running payroll and managing employee benefits out of HR’s scope.

Parker and his team expect three things of their HR function:

• Executing on legal compliance and employment law
• Getting involved in making managers better
• Having a point of view on who’s not good, and making sure managers are firing them fast
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Driving Accountability at Scale

• Through ~2000 employees, Rippling dug into ‘streams of anecdotes’ in Slack following negative customer feedback, won and lost opportunities, and churned customers. 
• Data and dashboards don’t make it clear what questions to ask – they lack the context that studying multiple individual interactions can provide. Anecdotes help you understand “why” areas are broken. 
• To codify this, one of Rippling’s core leadership principles is ‘Go and See’ – starting all the way down and using firsthand observations from individual successes and failures to solve problems. 

Tactic: Parker’s Framework to ‘Go and See’

• Parker sets up real-time streams recording customer anecdotes in public Slack channels to create visibility and accountability. 
• These channels record and echo pipeline developments or any support interaction rated negatively:
  
  • Negative NPS score
  • CSAT thumbs-down
  • Movement to a higher ‘churn score’ recorded by Rippling’s account management team
• Each interaction is posted with relevant context including:
  
  • Who is the customer?
  • What notes does the company have on the customer?
  • Links to the associated ticket and any supporting documents
• He values anecdotes over top-down metrics, and believes detailed stories reveal more actionable insights. 
  
  • When something is broken, he reviews the last 15–20 relevant interactions (e.g., Gong calls, support chats) to identify patterns and root causes.
• In the early days, he personally responded to issues in Slack, tagging CSMs or account owners to drive a culture of ownership.
  
  • The team quickly understood that they were racing Parker to respond, and that if the CEO got there first, it was a failure on their part. This helped embed “Go and See” as a cultural trait.

How Parker Stays Close to Product and Engineering Teams

• Parker holds ~60 quarterly planning meetings with different teams covering individual products and countries or platforms with a sales presence.
• These meetings are focused on diagnosing problems and pushing teams to align on near-term execution plans.
• He doesn’t let teams focus on more than two quarters out – companies are dynamic and plans change. 
• Rippling is a multi-product company – these meetings help Parker push product teams to think of themselves as standalone offerings (like their ATS product) that should succeed independent of the platform’s success. 

Tactic: Parker’s Approach to Quarterly Planning Meetings

• Parker uses one spreadsheet to plan quarterly meetings across all ~60 initiatives.
  
  • Here’s a blank template modeled after Parker’s Quarterly Planning Tracker
• Before most of these meetings, Parker provides comments in the spreadsheet on:
  
  • Areas of concern or frustration
  • Strategic questions that require diagnosis or resolution
  • Topics to focus on for the quarter
• Each team then prepares and links their quarterly planning decks for the next two quarters covering:
  
  • Quarter-to-date retrospectives 
  • Discussion topics based on Parker’s notes
  • Responses to flagged issues from the previous quarter
• Key topics in these meetings include:
  
  • Engagement & Adoption Metrics
    
    • Example: ATS setup flow completion rates
  • Strategic Product Gaps
    
    • Example: Selling ATS as a standalone product
  • Budgeting & Headcount Planning
  • Customer Support Heath 
    
    • Example: volume of issues, backlog tracking, JIRA metrics
  • Core Metrics 
    
    • Example: ARR (by product and suite level), win rates, attach rates, penetration rates
• Parker goes through each deck and leaves further comments for each team
• Purpose and Outputs of this process:
  
  • Teams align on near-term execution goals and are held accountable for past goals, key strategic issues get addressed quickly, and product teams are pushed to improve their offerings independent of how the rest of the platform is doing

Remote Work Requires Proactive Employee Oversight 

• Parker believes remote employees consistently show lower performance ratings, higher involuntary attrition, and worse retention. 
• Remote work is tolerated out of geographic necessity – Rippling has no French office but significant product and implementation work for French customers, necessitating remote French teams.
• Device-level visibility into employee activity can reveal significant non-work activity. Flagging behavior indicating that an employee may have “one foot out the door” can help managers assess where more scrutiny is needed within remote teams.
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Small Teams are Temporary; To Win You Need to Scale

• AI startups are currently operating in an unusually greenfield, early market—but that window is closing fast.
• Today, it’s still possible to scale revenue with a small team in AI – there are few dominant vendors and low competitive pressure. Once competitors catch up, prices will race to the bottom.
• AI companies can’t scale with lean headcount forever – to interface with the world, teams need people across sales, support, and marketing.
  
  • Rare exceptions exist for companies in markets others initially ignore or with large enough network effects to keep competition out. 
• Parker warns against scaling prematurely: at the ~200 employee mark, people who join don’t care about the business. 
• Scaling should follow finding product-market fit, when the business has a clear growth trajectory and unit economics are defensible. 

"Ultimately, you will need to build a giant team. Just not until your business is really indestructible."

Deeply Understanding Your Metrics Becomes Your Advantage

• Parker suggests targeting 10-12% of revenue for customer support at scale for SaaS companies. 
  
  • <10%: Underinvestment and harming retention 
  • >12%: Gross margins collapse – the company is no longer operating as a software business
• Rippling holds itself to an 18-month CAC payback (all-in, margin-weighted).
  
  • Median in public markets is at a historical high at ~28 months – this should not be the bar
  • Most startups calculate payback period wrong. True CAC includes burdened gross margin and real COGS.
• A deep understanding of these metrics gives teams a clear lever for scaling—unlocking new growth opportunities that investors are more likely to back.

"If you're in a place where you're like, we can scale Everest without hiring anyone to do it, you're aiming too low."

The CEO’s Job is to Champion Speed 

• As companies grow, everyone other than the CEO wants to slow down. The CEO drives the pace of execution and is the only advocate for speed. 
• Insisting on an "unreasonable" pace differentiates great companies from mediocre ones.  

Example: Parker’s ‘CEO in a Box” Traps

• Parker warns against “CEO in a Box” tradeoffs—when leaders present binary choices (e.g., “Do you want A or B?”), assuming both can’t be done. In reality, these either/or choices are often personal preferences masked as necessity.
• Parker’s default response is: “Why not both? Show me the law of physics that makes this impossible.”
• Trade-offs between speed and quality are a common example. Parker points out that slow teams are rarely high-quality, and that speed actually often correlates with a better understanding of the problem.
• The CEOs role is to break these default compromises – no one else in the org will keep up the pressure to go faster while doing more.

What it Means to be a Platform-First Company 

• Many customers’ deepest problems are cross-functional – Rippling can solve a higher class of problems for customers by building a broader suite of more seamlessly and deeply integrated interoperable applications. 
• Rippling’s platform-first approach decomposes business software applications into a set of underlying constituent parts (permissions, workflow automations, analytics, custom objects, configurable views, approvals, super groups, and documents) that are reused. Rippling can afford to build more deeply than their competitors in each of those parts, allowing them to win on underlying capabilities across every application they build. 
  
  • Companies that build "artisanal software” cannot afford this depth of investment in their underlying platform in the way Rippling can. 
• This approach requires people who take real ownership over each product area. Rippling has solved this problem by staffing products initially with small teams led by former founders.

Example: How Parker Uses Former Founders to Build New Products

• Rippling hires former founders as GMs of new product areas, giving them full ownership. 
  
  • Giving GMs autonomy prevents executive attention from becoming a bottleneck within Rippling – GMs are individually responsible for their product’s development and success.
  • This autonomy means GMs have to recruit their own early teams and build from scratch, but have access to Rippling’s internal design resources and frontend development teams.
• These leaders are incentivized by the opportunity to focus on building products while Rippling handles distribution.
  
  • Distribution was a key pain point for many of their acquihired founders. 
• Rippling’s “platform-first” philosophy means these GMs can build faster and better with shared underlying components (permissions, workflows, analytics, etc.) that allow platform leverage to compound with time.
  
  • Now products launch faster and hit $1M+ in ARR in weeks, not years. 
• The model works because standard build cycles (5–10 engineers, 18–24 months) now produce apps that are more competitive day zero than prior generations.
  
  • Rippling tracks time-to-$1M and time-to-$10M ARR—newer products consistently outperform old ones.

Example: How Rippling Platformizes Shared Services to Build Winning Products

• Documents:
  
  • Began as a small internal tool but became a core dependency across multiple products (onboarding, HRIS, compliance).
  • Product teams within Rippling were often waiting on document-related features or fixes—creating a bottleneck that inspired spinning Documents out into its own product team with a dedicated GM. 
• Permissions & Approvals:
  
  • Most software permissions default to no access, forcing users to ask others for help.
  • Rippling’s platform uniquely allows their product to be opinionated by default. 
    
    • Their platform defaults to assigning reasonable permissions based on an employee’s role, function, and org chart position.
    • As people move roles, their permissions automatically update based on their job function, not the individual.
  • Approvals often closely follow org chart information and job functions
    
    • Rippling’s platform allows for better approvals routing given their existing platform context