👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help founders fall in love with building their companies again. Learn about working 1:1 here.

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Hi there,

It’s great to be back in your inbox. I had to miss last week’s newsletter because I was sick for a week! 

The old me would’ve tried to power through, keep all my commitments and send out a newsletter anyways. The new me is learning to surrender and listen to my body, even if it means “letting people down” and “losing momentum” which is what my inner critics worry about.

I wrote about navigating these feelings on LinkedIn. 

Today we’re back on team building (if you missed the last few newsletters, catch up here on topics like navigating performance issues, running high impact 1:1’s and hiring). 

Specifically, we’re talking about how to design a compensation policy for your startup.

We’ll cover:

• Designing an aligned comp policy that can scale

• How to make decisions around raise requests and comp policies

• Team building wisdom from a founder who scaled and exited her content agency

Let’s dive in.

Where we go deep on the outer work or the inner work of building a startup.

How to Pay People Intentionally

Let’s be honest: compensation is a loaded topic.

Money is rarely just about numbers. For many of us—and our employees—it’s tied to our sense of worth, safety, and security. That’s why conversations around pay in a startup context can often feel heavy, emotional, and confusing.

I saw this often as a founder and continue to see it in my coaching practice. 

(When we shift to the inner work, we’re going to talk ALL about the feelings that come around this.)

Having a values-aligned compensation policy to ground yourself in can make all the difference.

The right policy reflects your company’s values, your leadership philosophy, and the relationship you want with your team. It gives you clear guardrails when navigating offers, raises, and benefits —so your decisions feel consistent and grounded, not reactive.

Today, we’ll cover how to build a compensation strategy that’s fair, transparent, sustainable, and emotionally intelligent—so you can reward your people meaningfully, without burnout or resentment.

1. START WITH A VALUES-ALIGNED PHILOSOPHY

Before setting numbers, define your compensation philosophy:

• What do you believe about money, equity, and value creation?

• How do you want people to feel when they receive your offer or comp package?

• What does “generosity” mean to you—and where is the boundary where it turns into resentment? (Inquire: are you giving from obligation, fear, or genuine choice?)

Create a short written statement that outlines:

• Your principles (e.g. transparency, fairness, market awareness, sustainability)

• What you reward (e.g. impact, ownership mindset, collaboration)

• How comp may evolve as the company grows

E.g. “We aim to pay fairly and generously within our means, balancing market data with our mission, values, and runway. We offer profit-sharing so everyone shares in the value we’re creating together.”

2. DESIGN COMPENSATION THAT WORKS FOR NOW AND THE FUTURE

Take stock of your current business reality:

• Runway and revenue

• Team size and roles

• What “good” looks like in each role

• What you can afford

From here, create your baseline structure:

• Cash compensation: Use market data (Pave, Levels benchmarks) to anchor decisions (you can consider incentive comp where it makes sense for certain roles)

• Equity: Create equity bands by level and role; clarify vesting, cliffs, and dilution (or for other ownership-based comp, look at profit sharing)

• Total comp: Consider not just salary + equity but L&D, PTO, benefits, and flexibility

Don't try to be everything at once. Build your comp like a product — start with an MVP, refine over time.

3. BUILD THE WHOLE PACKAGE: TANGIBLE + INTANGIBLE

Your total compensation offering should reflect more than salary. Here are a few examples of additional items you could pull in, based on values and company needs:

• Equity: Teach employees what it means to own equity (more below)

• Profit-sharing: To allow employees to be rewarded for the value they’re creating in the shorter term (potential alternative to equity)

• Benefits: Health, dental, mental health stipends, wellness reimbursements

• PTO policy: Thoughtful policies like:

  • Summer Fridays

  • Company-wide closures around holidays and long weekends

  • Birthdays off

  • Minimum time-off (vs. unlimited, which can lead to guilt and burnout)

• Remote + Flex work: Define expectations clearly — e.g., “core hours” or async norms

• Learning & Development: Budget per employee (e.g. $1k/year), coaching stipends, or access to peer learning

• Parental Leave: Build a policy early, even if no one’s expecting yet 

These offerings can often be more meaningful than a slightly higher salary, especially to mission-driven talent (and they’re more efficient from a tax perspective).

4. EXPLAINING EQUITY WITH CLARITY

Most early startup employees don’t fully understand stock options. Use plain language, metaphors, and visuals. Include:

• What are options vs shares

• Strike price, vesting schedule, cliff

• How to exercise and what that costs

• Potential upside (and the risk!)

Make a simple equity explainer doc or Loom video as part of onboarding.

Also consider offering choice: cash vs equity-heavy packages (e.g., someone might choose $90k + 0.2% equity or $80k + 0.4%). This gives people agency and helps align expectations.

5. MANAGING COMP REQUESTS WITH INTEGRITY

When someone asks for more money:

1. Listen deeply: “Thanks for bringing this up. Can you walk me through what’s motivating the request?”

2. Clarify your own position: Are you in resentment or choice? In scarcity (fear) or abundance (possibility) mindset?

3. Evaluate impact: Does this person’s work materially impact business outcomes?

4. Reality-check the budget: Can the business sustain this?

5. Get curious and creative:

   1. Is there a performance-based raise timeline?

   2. Could you structure a bonus tied to outcomes?

   3. Is there an equity bump possible if cash is tight?

   4. Are there L&D or coaching investments that would also feel like growth?

Then reflect and respond with honesty and clarity, not defensiveness.

6. DECISION-MAKING FRAMEWORK FOR POLICIES (E.G. PARENTAL LEAVE, REMOTE WORK)

Use a 4-part lens when designing policies:

• Company Values: What feels most aligned?

• Employee Needs: What do your people need to feel safe, cared for, and to thrive?

• Financial Impact: Can the business sustain this? How would it scale?

• Market Research: What do peers and competitors offer?

You don’t need to “match” Google, but you do need to make intentional, principled decisions, and communicate the why behind them.

7. BE TRANSPARENT, EVEN WHEN IT’S INCOMPLETE

Clarity creates trust. If you’re not doing salary bands or formal leveling yet, be honest about where you’re at, what’s coming next, and what principles are guiding your decisions.

Transparency doesn’t need to mean sharing everyone’s comp — it means being open about how decisions are made and what team members can expect.

8. CHECK IN WITH YOURSELF AS A FOUNDER

Ask:

• Am I leading comp decisions from fear, guilt, or people-pleasing? Or from values, vision, and generosity? 

• Is our policy building trust or confusion?

• Am I building something sustainable for both me and my team?

It’s possible to pay well and protect your own well-being and business health.

FINAL WORD

Compensation is one of the most emotionally loaded, high-impact leadership decisions you’ll make. It’s also an opportunity to lead with clarity and compassion — to reward your team, set sustainable boundaries, and build a culture where people feel seen, respected, and aligned.

You don’t have to be perfect. But bringing intentionality and principle to your strategy helps.

FOUNDER INSIGHT: SHINDY CHEN

Today’s expander is Shindy Chen, currently Founder of Content Barn and formerly Founder & CEO of Scribe, a financial content agency she grew to a profitable company with 4 full-time staff and 30+ contractors, and then exited.

I had a chance to ask Shindy to share her team building wisdom with me and I’m excited for you to hear what she has to say.

What advice do you have for founders around compensation?

Pay someone as much as you can afford; more often than not what you’re paying for is their skillset and value-add that will only ultimately increase the value and efficiency of the overall company.

Don’t skimp on compensation - top talent is worth its weight in gold.

What wisdom can you share around delegation and giving up control as a founder?

There’s nothing better than giving your employees the autonomy to make key decisions and problem solve on their own, albeit with clear instructions, directives, and guidelines in place. 

People want to feel like their work has an impact; when you delegate tasks or decisions, this gives them a chance to make significant contributions and they may even surprise you with their resolve and drive. 

This in turn frees up your time so you can focus on bigger picture company decisions. Work less in the company, work more on it.

What does authentic leadership mean to you? 

Transparency, integrity, common sense, and leading by example. 

For example at Scribe we had a “way of work” document that included our values, tenets, and attributes of company culture, like “avoid meetings just to have meetings.” 

I feel a leader should also at least understand the nuts and bolts and operating systems of a company; not to master everything per se, but to at least know how and why their teams follow a certain protocol or use a certain software. That way they can better understand how to lead people through change if/when change becomes necessary.

To learn more from Shindy, you can follow her on Substack, Instagram and LinkedIn.

I’m currently building out The Within Resource Library — a database of all of the recommendations I’ve made in this newsletter and that I regularly make to my clients —be it podcasts, books, newsletters, templates, courses or practitioners to work with.

Have a great recommendation to share with this community?

Reply to this email and let me know, and I’ll make sure to send the resource library your way when it’s complete.

• 1:1 Coaching: I want to help you fall in love with building your company again. Book a free coaching consultation to learn how we’ll work together on this.

• Let’s be friends: If you want to see more of the BTS of building Within and receive more tips and ideas on building with integrity, connect with me on LinkedIn and Instagram.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Thanks for your presence and feedback.

With love,
Roslyn 💚