Scaling in 90 Days: The HR Playbook for Efficiency, AI, and Leadership

How should HR leaders scale efficiently in private-equity-backed environments? Kelly Oliver shares lessons on revenue alignment, manager readiness, and leading AI without losing human connection.

Kelly
Oliver
Executive Advisor

Episode chapters

00:00 | Intro: Leading HR in PE-Backed, High-Pressure Environments

01:58 | Meet Kelly Oliver: From Engineering to Head of HR.

04:00 | The Real Question: How Do You Scale an Organization Efficiently?

06:07 | Why Everything Is Now a 90-Day Window

08:56 | HR’s Role in Revenue-Driven Execution

11:35 | Performance Heat Maps and HR’s Early Warning Signals

12:31 | Why Every HR Team Should Run a QBR

17:56 | Managers Are Unprepared & Here’s Why

19:28 | Manager 101: What Leaders Actually Need to Learn

21:36 | Managing the “What” vs. the “How”

27:27 | How AI Is Already Changing the Manager Role

29:08 | Where AI Belongs: Back-End Efficiency, Not Front-Line Humans

32:14 | Why HR Must Be Central to AI Strategy

35:02 | AI Literacy for HR Leaders: Lean In or Fall Behind

38:02 | Human Connection Still Matters More Than Ever

40:46 | Final Challenge: Be Better Than a Bot

Show summary

In today’s private-equity-backed environments, HR leaders are operating under a new set of rules. Growth is no longer measured in years or even quarters — it’s measured in 90-day windows. Revenue expectations are tighter, efficiency matters more than ever, managers are underprepared for the pressure they face, and AI is rapidly reshaping how work gets done.

In this episode of Pulse by HRBench, Logan Rivenes sits down with Kelly Oliver, a seasoned HR and business leader with nearly 30 years of experience spanning engineering, information systems, and senior HR roles at Microsoft, Oracle, HP, Salesforce, and most recently as Head of HR at a PE-backed cybersecurity company.

Kelly brings a rare lens to the conversation — one that blends systems thinking, revenue awareness, and deeply human leadership. Together, they unpack what HR leaders must do differently to stay relevant, credible, and impactful in today’s high-stakes operating environment.

Scaling Efficiently Starts With Looking Inward

One of Kelly’s central themes is that scaling efficiently today requires a fundamental mindset shift. Instead of constantly looking outward — adding programs, tools, or headcount — organizations must look inward and scrutinize their internal processes.

Kelly compares this moment to marathon training. When preparing for a race, runners don’t add complexity — they strip away everything that doesn’t serve the goal. Nutrition, rest, recovery, and scheduling all come under close examination. The same principle applies to organizations trying to scale efficiently.

For HR leaders, this means asking hard questions:

  • Which processes directly support revenue and execution?
  • Which initiatives are “nice to have” but don’t serve the company’s most urgent goals?
  • Where can friction be removed to help teams move faster?

In PE-backed companies especially, efficiency isn’t optional. The pace of change is accelerating, and organizations must be lean enough to pivot quickly without breaking trust or execution.

The Reality of the 90-Day Operating Window

A major shift Kelly highlights is the compression of planning cycles. Quarterly forecasts are increasingly managed month-to-month and even week-to-week. Goals that once spanned half-years are now expected to be achieved in 90 days.

While this cadence increases urgency, it also creates friction — especially around talent development. Skills can’t always be built, demonstrated, and mastered within a single quarter. HR leaders must help executives set realistic expectations while still delivering progress.

Kelly emphasizes the importance of “muscle memory” during these compressed cycles. Leaders who have navigated high-growth, high-change environments before are better equipped to communicate clearly, manage change, and stay transparent under pressure. HR plays a critical role in identifying and enabling those leaders.

Why HR Must Get Closer to Revenue

A defining throughline of the conversation is the idea that HR must deeply understand how the business makes money.

Kelly is direct: quarterly goals are about revenue. While engagement surveys, performance reviews, and HR programs matter, they are not the primary objective in high-growth environments. HR leaders who don’t understand the P&L, cash flow, and revenue levers risk misalignment with executive priorities.

She encourages HR professionals at every level to build relationships with finance counterparts and ask fundamental questions:

  • Where does HR’s work show up on the income statement?
  • How does workforce performance impact revenue outcomes?
  • When sales goals change, how should HR priorities shift?

This revenue literacy enables HR to adjust timing, sequencing, and scope of initiatives in ways that support the business — not distract from it.

HR as an Early Warning System

One of the most tactical insights Kelly shares is HR’s ability to act as an early warning system for revenue risk.

By maintaining visibility into individual performance — particularly in go-to-market roles — HR can surface leading indicators before problems hit the forecast. Performance heat maps, manager feedback, and regional trends can reveal uncovered quota or declining productivity long before quarterly results are finalized.

Rather than viewing performance management as purely a managerial responsibility, Kelly positions HR as a strategic partner that helps leadership connect people data to revenue outcomes.

Why Every HR Team Should Run a QBR

Kelly makes a strong case for HR-led Quarterly Business Reviews.

Instead of treating QBRs as purely financial or sales-driven exercises, HR teams should mirror the business’s QBR structure and apply an HR lens to it. This includes reviewing:

  • What’s going well and what isn’t — and why
  • Key business KPIs alongside HR metrics
  • Talent implications tied directly to business performance

Running HR QBRs builds data literacy, aligns HR with executive language, and reinforces credibility. It also helps HR teams practice tying insights to evidence, rather than intuition alone.

Managers Aren’t Prepared — And That’s a Systemic Problem

As the conversation shifts to people leadership, Kelly is candid: many managers today are unprepared for the environments they’re operating in.

Organizations expect managers to scale at the same pace as the business — often without adequate training. Employees are promoted from individual contributor roles into people management positions, sometimes jumping from two direct reports to twenty, with little to no enablement.

Kelly calls manager training a non-negotiable. Manager 101 should not be confused with onboarding. It must focus on:

  • How leadership works at this company
  • How values show up in day-to-day decisions
  • How to sit in discomfort and handle people issues directly

Avoiding discomfort by outsourcing sensitive conversations to HR weakens both managers and the employee experience. Growth, Kelly argues, happens through discomfort — and managers must build that muscle early.

Managing the “What” vs. the “How”

A key distinction Kelly draws is between managing what work gets done and how it gets done.

The “what” — deadlines, tasks, outputs — can increasingly be automated. The “how” — values, behavior, communication, empathy — cannot.

Great leaders observe how their people work, provide direct feedback, and model values in action. These skills become more important, not less, as organizations grow and technology advances.

AI, Efficiency, and the Human Connection

AI is one of Kelly’s biggest passions, and her perspective is grounded rather than alarmist.

She believes AI will continue to automate large portions of work management — but leadership and human connection cannot be replaced. The risk isn’t AI itself; it’s losing empathy, trust, and connection in the pursuit of efficiency.

Kelly advocates for placing AI “in the back of the house” first:

  • Automating clunky internal processes
  • Streamlining HR systems like payroll and benefits
  • Reducing friction that slows employee productivity

In HR, employees are the customer. Bombarding them with AI-driven interfaces without thought risks the same fatigue seen in AI-fueled sales outreach.

Why HR Must Be Central to AI Strategy

Excluding HR from AI strategy, Kelly argues, is a serious mistake.

HR systems shape the employee experience — and inefficient HR processes directly impact productivity, retention, and revenue. Payroll confusion, benefits issues, and slow workflows create friction that ultimately costs the business money.

AI strategy should be a cross-functional effort involving HR, IT, and operations, with a clear focus on employee-critical processes.

Be Better Than a Bot

As the episode closes, Kelly leaves listeners with a simple challenge: be better than a bot.

AI can offer advice, structure, and efficiency. But it cannot replace eye contact, empathy, or authentic leadership. Human connection remains one of the strongest antidotes to burnout and disengagement — and one of the most important leadership skills of the future.

For HR leaders navigating PE-backed environments, the mandate is clear: understand the business, enable managers, embrace AI thoughtfully, and lead with humanity.

Because in a world increasingly shaped by automation, the leaders who stand out will be the ones who remain unmistakably human.