The Road To: Scaling Your People Ops and HR Department

Building a strong People Operations (People Ops) function is critical for the success of any startup, but what if you’re operating with a small team or no dedicated People Ops professionals at all? For startups that are just starting to scale, managing HR responsibilities can feel overwhelming. From recruitment and onboarding to compliance and culture building, it can be tough to juggle all the tasks while maintaining focus on growing your business.

In this blog, we’ve gathered some of the most insightful sessions from Startup Boston to help you navigate People Ops at an early stage. Whether you’re working as a team of one or managing a rapidly growing startup, these expert-led panels and discussions will help you understand the key HR functions you need to address, when to bring in People Ops professionals, and how to scale effectively without breaking the bank.

Table of Contents: 

1. People Ops 101: How to Manage at a Startup without an HR Team

2. Team of One: Building a Scalable People Ops Operations

3. Location, Location, Location: How Much Facetime is Needed?

4. How to Scale from 10 to 100 Employees When You Are Too Busy to Hire

5. CPOs and CEOs: How to Find and Nurture a Shared Vision and Relationship

6. Finding Balance: Preparing for Layoffs or Hiring Freezes in the Tech World

7. Finance Fundamentals for Non-Finance Folks: What to Know and How to Grow

8. Chutes & (Career) Ladders: Architecting a Scalable Comp Plan

9. How to Create and Sustain a DEI Strategy on a Budget

10. Mergers & Acquisitions: So You’ve Been Acquired, Now What?

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People Ops 101: How to Manage at a Startup without an HR Team

What questions do you have about building HR functions without a dedicated People Ops team? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• The most important HR functions your company needs to address

• Which job functions can be outsourced and which should stay internal

• Resources for companies without an internal HR team

• When it’s the right time to make your first People Ops hire

• What to look for when hiring your first People Ops employee

Speakers: Pooja Samuel, Ahfeeyah Thomas, Shea Coakley, Tracy Tsubokawa, Cristina Costa  

Team of One: Building a Scalable People Ops Operations

What questions do you have about building out People Ops infrastructure as your startup grows? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• How a team of one can build a People Ops tech strategy that grows with the company

• Ways to automate manual tasks with tech on a limited budget

• How to encourage hiring managers to take ownership of sourcing and marketing roles

• Developing a Learning & Development strategy with limited resources

• Encouraging managers and leaders to make learning and development part of the culture

• Best practices for peer-to-peer learning in startups

Speakers: Abbey Cohn, Grace Tkach, Christina Wang, Samantha Yancich, Amanda Lewe 

Location, Location, Location: How Much Facetime is Needed?

What questions do you have about evolving workforce structures and transitioning between formats? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• How startups decide where and how people work

• The “why” behind transitions from one workforce format to another

• The “return to work” trends and how startups are shifting from virtual to increased face-time

• The benefits of different in-person, virtual, and hybrid models

Speakers: Joseph Arquillo, Courtney Utsey, Barbara Donnelly, Paul Carelis

How to Scale from 10 to 100 Employees When You Are Too Busy to Hire

What questions do you have about scaling your startup and growing your team quickly? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• How to disengage the brakes on your headcount and manage rapid growth

• How to maintain quality and culture while scaling your team

• Strategies for attracting and retaining top talent

• The tradeoffs of managing your scale moment in-house versus utilizing staffing firms

Speakers: Jody Robie, Michael Brown, Danny Karageorgis, Emily Barden  

CPOs and CEOs: How to Find and Nurture a Shared Vision and Relationship

What questions do you have about ensuring alignment between a CEO and HR leader? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• Key questions an HR leader should ask a CEO during the interview process to gauge if there is a fit

• How to effectively inquire about the CEO's vision for the company and evaluate alignment with HR goals and values

• How to gain insights into how potential future disagreements with the CEO will be handled at the startup before accepting the offer

Speakers: Stefanie Bishop, Mike Greene, Francis Rhodes

Finding Balance: Preparing for Layoffs or Hiring Freezes in the Tech World

What questions do you have about managing layoffs and hiring freezes with care and professionalism? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• How to effectively plan and carry out a layoff or hiring freeze—from initial considerations to final implementation

• Best practices for communicating layoff news or hiring freezes to employees and strategies for providing support during the transition

• Understanding why organizations might rehire for similar positions shortly after layoffs and how to manage public reputation and internal morale in the aftermath

Speakers: Sandra Ma, Nate Aune, Abbey Newmark, Colin Navon 

Finance Fundamentals for Non-Finance Folks: What to Know and How to Grow

What questions do you have about strengthening your financial acumen as an HR or People Ops leader? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• Why HR needs to understand the business’ financials

• How to become a good partner to your Finance team

• Key financial terms and topics HR should be familiar with

• Important financial metrics HR should understand and why

Speakers: Katie Fifer

Chutes & (Career) Ladders: Architecting a Scalable Comp Plan

What questions do you have about creating a compensation strategy that attracts and retains talent? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• How startups should approach creating a compensation philosophy, especially with a remote/hybrid workforce

• How your career ladder and compensation philosophy should support the company’s strategic goals

• How People Ops professionals can gain leadership buy-in for the compensation plan

• What data sources are helpful for gaining compensation market information

• How teams can evaluate the effectiveness of the compensation strategy

Speakers: Trisha Feldman, Gabriela Serret-Campos 

How to Create and Sustain a DEI Strategy on a Budget

What questions do you have about building a diverse, equitable, and inclusive organization on a budget? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• How to create a truly diverse, equitable, and inclusive organization without breaking the bank

• How to ensure full participation and mutual power across racial, economic, and cultural identities

• The importance of intentionality and commitment in fostering inclusion

• Why DEI should remain a priority, even in times of economic change and tightening budgets

Speakers: Sonya Mack, Amy Flynn, Jonathan Myers 

Mergers & Acquisitions: So You’ve Been Acquired, Now What?

What questions do you have about navigating an acquisition? We’ll be answering the questions you’ve always wanted to ask. In this session, we’ll also cover important topics such as:

Topics Covered:

• What are the varying levels of information transparency versus uncertainty during an acquisition?

• How does access to knowledge change the experience of an acquisition?

• What are the change management impacts of acquisition, and how do you prepare your employees and managers for this change?

• What do different types of mergers and acquisitions mean for equity/stock?

• What people trends tend to occur after acquisitions?

Speakers: Dipti Salopek, Anik Conley-Das

As you navigate the challenges of building and scaling your People Operations function, it’s important to stay proactive and continue refining your approach. Whether you’re managing HR responsibilities as a team of one, automating manual tasks with tech, or developing a solid L&D strategy, the key to success lies in learning from those who’ve been there before and staying adaptable to the needs of your growing startup.

By implementing the insights shared in this post—from building a strong HR foundation to making your first People Ops hire—you’ll be well-equipped to create a positive and scalable workplace culture. Keep refining your people strategies, leveraging tools to streamline processes, and fostering an inclusive environment that attracts and retains top talent.

For more tips and expert advice on managing People Ops at your startup, be sure to subscribe to our newsletter below. Stay ahead of the curve and continue building a solid HR infrastructure that supports your startup’s growth and success!