Kathryn O'Day

Are You Behind on Scaling?

I often hear from CEOs of high growth companies that they need process, operational help, or they feel “behind” on scaling.

Good news: THIS IS TOTALLY NORMAL!

If you’re “ahead,” there’s a good chance you built process before you needed it, overhired, or aren’t growing fast enough.

I’ve seen operational scale and systems at high growth companies of all stages and sizes.

What I’ve learned:

1. Every company is unique. Scale and operational needs can differ wildly based on founder personality, industry, product, and customer needs.
2. There are common patterns of what things scale and when.
3. Even when you’re on track, things feel messy and imperfect.

So, what are the stages of scale and key characteristics?

6 Stages of Operational Scale at Startups

STAGE #1: Wild West

Key Characteristics:

• Everyone reports to the CEO
• “Communication” means turning around in your chair and talking to each other
• Everyone is in every Slack channel
• Job titles? What are those?

##Protip: Many founders look back on this time as one of their favorite phases. It’s hard but incredibly focused. Nothing matters but customers, revenue, and building something people want. Lots of hilarious stories about scrappiness and first-timer mistakes.

STAGE #2: The Basics

Key Characteristics:

• Employee growth from 10 to 50
• Adding one layer: managers or team leads for functional areas
• Intentional communication (Weekly Update Email, All-Hands Meeting)
• V.1 of hiring process, performance management, goal setting
• Wrangling — uh, I mean— bringing consistency to contracts, invoices, and pricing
• Workflows for high priority items like inbound leads

##Protip: Define your Core Values and shore up your culture NOW! It will help in recruiting, hiring, performance management, and faster decision making across the company.

STAGE #3: Departments Grow Up

Key Characteristics:

• Largest teams have 30+ people
• Adding managers of managers including more external hires
• More documentation, process, training, and planning within each department. Examples:
• new sales rep bootcamp
• customer success internal wiki
• engineering team offsite
• Upgrading internal tools or software for more automation, volume, complexity
• Adding “rules of engagement” between departments and playbooks for cross-functional projects like product launches

##Protip Invest in your people. Leadership training and career path discussions are fantastic to implement now. Employees feel empowered and see a future at your company, even if they get a new boss or their day-to-day has changed.  

STAGE #4: Big Kid Stuff

Key Characteristics:

• First foray into global expansion, launching a new product, moving up or down market, opening a new office
• Bringing services in-house like legal, IT, facilities management
• Shoring up product and business security, governance, compliance and other things with checklists, paperwork, and lawyers 😉  

##Protip Any senior leaders or folks from the early days looking for new challenges? Having trusted people on new initiatives can provide them with “startup-like” work within a larger company. It also ensures company culture is at the forefront and de-risks the people aspect of the new endeavor.

STAGE #5: Operations Everywhere!

Key Characteristics:

• More operations-specific hiring than ever before
• Company-wide understanding of the need and value of operations
• Centralized ops function -OR- each dept will have a dedicated ops role or team

##Protip Who on your current team is organized, analytics-oriented, and loves playbooks and systems? Could they be a fit for a new operations role?

STAGE #6: Repeatable Expansion

Key Characteristics:

• Are you even a startup anymore?!? 😜
• Dedicated teams for new location openings, M&A, new market launches
• You’re thinking about unicorn status, going public, SPACing…and the fun new challenges that come with it!

##Protip Appreciate how many lives you’ve impacted. Hundreds, possibly thousands, of people with jobs, opportunities, life experiences, relationships, and memories, thanks to what you and others have built.

Every Company Is Unique

These stages are an overview but each company is different.

At Pardot, we opened up a London office before we had in-house legal or IT. Some companies make their first acquisition before they’ve hammered out their hiring process. Sometimes Stage #5: Operations Everywhere! happens as part of Stage #3: Departments Grow Up. Or not at all!

What operational stages or journeys have you seen? Do you identify with these? Any key areas to add??

Awesome Men Who Want to Help

I’ve worked with many fantastic men in leadership positions who have been supportive of me and other women at the company and in the business world at large.

I’ve also talked to many men who care and want to help but aren’t sure where to start.

If you’re a man in a leadership role who wants to help level the playing field or help more women succeed, here are 6 specific strategies that are straightforward and impactful.  

Some of them you can do in less than 5 minutes, starting today!

6 Ways Men In Leadership Roles Can Support Women

1. Give them access.

A (male) CEO I worked for introduced me to an informal group of CEOs with an email list and a quarterly gathering. He was too busy to regularly participate. For me, it was an incredible learning and networking experience. The group wanted more diversity and welcomed me as a startup executive even though I wasn’t a CEO.

💡✨ What exclusive or high-impact organizations or events could you broker access to for a woman at your company?

2. Open the door.

The first week I joined the company, the (male) CEO sent me an article detailing the toxic bro culture of Wall Street and said, “If our company is ever doing things like this, let me know.”

There were a few things over the years I brought to his attention. Nothing egregious. A comment to a woman about what to wear to a meeting. A suggestive email from a customer. He addressed them quickly and directly. Molehills never became mountains. The women who worked for him proudly shared the stories with their friends and future hires.  

💡✨ Do the women at your company know you want to hear from them if something is off? Shoot them a quick note linking to this blog or another article about the topic.

3. Advocate for good parental leave.

Not just primary parent leave, which we know is important, but secondary parent leave too.

For example, when Dad has more time to help with a new baby because of secondary parent leave, Mom has more mental and physical energy to re-engage with work. The time Dad spends as primary caregiver lays the foundation for a more equitable split of family responsibilities in the future. Subsequently, Mom is more likely to stay in the workforce.

This heterosexual example is not coincidence. It’s a much more common dynamic in male/female relationships than same sex ones.

💡✨Are your company policies supportive of working parents which directly and indirectly provide tremendous support for working moms?

💡✨ BONUS ✨💡 Did you take your full paternity leave? If you do it, it’s easier for the moms in your organization to do it too!

4. Make intros to mentors, especially women.

If you meet someone awesome who could be helpful to an up-and-coming woman in your organization, see if they’d be open to an intro.

Meeting experienced folks who feel “like me” – similar gender, ethnicity, role, disposition, or background – can be transformational to someone’s motivation, growth, and career trajectory.

If you don’t have many women in leadership currently, this is a great “hack” to provide mentorship to your future women leaders who you want to retain and develop.

💡✨ Could you make a meaningful intro?

5. Widen the hiring pool.

When you hire more women, the effect starts to snowball. Women recruit other women. Having women at your company attracts other women. Getting to critical mass of 30% will happen faster than you think.

The place to start… have more women in the candidate pool!

💡✨ Do you have at least two women as finalist candidates for each role?

6. Be mindful of social activities.

Outside-of-the-office social interactions are a great way to build rapport and network. Are these activities interesting, welcoming, and appropriate for the women at your company?

Coffee and lunch are fantastic networking for all. Group dinners are also good. Book clubs, bowling, and volunteer activities are also pretty universal.

If it’s a casual, typically “guy” event like a fantasy football league or sports bar after work, be intentional about inviting the women. They may be interested – in the event or the bonding.

💡✨ Can you adjust a social or networking opportunity to make it more welcoming to women?

Share other ideas!

These are just a few of many ways male CEOs or leaders can support women in their careers.

💡✨ What other ideas or experiences can you share to build on this list??

Special shout out to Craig Hyde, Rigor CEO, who inspired several items on this list. Thanks for initiating these things before I even knew I wanted them!

Startups + Career Growth = Magic

One of the most powerful things about a startup is the career and growth potential. You’re learning constantly, things are moving fast, the work changes daily, and the trajectory is unlimited.

I often get asked, “How did you become XYZ Role at Company ABC?”

Or, put another way, “How do you leverage the fast pace, flexibility, and chaos of a startup to turn it into a role and career that you love?”

Not every company has a Make Your Own Role option (love this, Laudable!) but if you’re intentional, you can build your own ideal role by doing work you enjoy that benefits the company.

7 Steps To Create Your Ideal Startup Role

1. Do your current job well.

Work hard. Do good work. Have a great attitude. You will build credibility, good will, and relationships across the company.

2. Identify company pain points or opportunities.

What could drive more revenue? Save money? Make customers happier? There’s usually at least 1,496,382 things a startup could improve.

3. Pick opportunities that interest you.

What problem is most interesting? Where do you have aptitude or experience that might be helpful? If you’re going to invest time, make it something you enjoy or want to learn.

4. Work it.

Start with a low effort, high value item. Think about revenue and what your company’s priorities are. Double check with your manager if needed. Then off to the races. Plan a user group, make a pipeline report, build a self-serve tool -- whatever you’ve picked at the intersection of company need + your interest.

5. Assess.

What did you learn? Did you enjoy the work? How was it received by the team? Use this analysis to determine your next foray.

6. Double down.

Continue experimenting. Figure out what you like. Do more of that. You’ll start to build an informal portfolio of projects and be the go-to person for those things.

7. Voila!

You’re doing great work that you enjoy while solving company problems. You’ve set yourself up for a custom role, possible promotion, and a meaningful career long term.

But Wait! 5 Things That Could Derail Your Ideal Startup Role

1. You’re too far ahead.

You love to lead sales trainings but you only have 2 sales reps. You want to sell to enterprise customers but your product is currently $100/mo. You want to deep dive on security protocols but the app is still in beta.

Keep the faith! Startups move fast and things could change quickly. A colleague of mine wanted to work internationally. At the time, we were a 100 person company in Atlanta so this seemed pie in the sky. In less than a year, we had been acquired and needed her skill set abroad. Startup dreams coming true!

2. What you want to do doesn’t drive revenue.

Or save money. Or help a LOT with efficiency or team morale. Make sure it’s valuable. Your passion for cat gifs, cooking, or yoga may be awesome but if it doesn’t help the bottom line, you probably won’t make much progress.  

3. Not doing your day job well.

I cannot emphasize this enough:

**Doing your current job is table stakes for future promotion or customization.**

Gotta do excellent work on the task at hand to have internal credibility. If the current role is truly not a fit, at least show you’re working hard, have a great attitude, and highlight what you are good at.

4. Waiting for an official job opening.

The best way to get a job is to already be doing it.

Position yourself to be top-of-mind when your company starts thinking about that role. It’s faster, easier, cheaper, and happier to hire from within!

Better yet, companies will often create unique roles because of a person on their team. They may not post online for a new hire operations specialist who also does lead gen but if you’re awesome at it, you’ll be the next Lead Gen & Onboarding Specialist.

5. Wanting it right now.

Startups move fast but there’s no time warp worm holes. Six months or a year can feel like a long time but in the grand scheme of things, it’s nothing! Starting over at a different company will take even longer. Don’t let impatience cloud your judgement or cause you to miss a rocketship ride.

This is one of my favorite topics and I’m often chatting with up-and-coming startup stars who want to understand how to maximize the opportunity. What other advice would you offer? What has worked for you?

Learn by doing

“The most effective way to do is to do it.”

It’s a favorite Amelia Earhart quote.

And life reminder.

I like to do pre-work. I clean my room before I study. I do laundry before I start projects. I manage my inbox before I eat the frog.

It took me a long-ass time to get this blog going. I was worried about the tag line, topics, tone. Am I funny? Serious? What do I write about?

All things b̶e̶s̶t̶ only figured out by actually writing.

Do the thing you want to do

You want to start a company? Don’t get an MBA, then join a startup, then be an investor. Just start a company.

You want to start a blog? You don’t need to learn to code, take a writing course, hire a branding expert. Just start a blog.

Experience is a great thing. You get experience as time passes. Isn’t it most helpful to get experience in the exact area you want experience??

The fastest way

When I ask my husband, a running coach, how to get better at running, he says, “Run.”

I want the answer to be:

• work on running form
• buy new shoes
• eat more vegetables

Can’t I get good at running without running??? Pleeeeeease.

But there’s no substitute for lacing up your shoes and putting in the miles. Or sitting down and writing. Or launching your first business.

The only way is through.

The fastest way is through.

Shout out to iwantthatmountain, founded by Ashley Gattis, where I found the gorgeous Amelia Earhart quote. It’s in our kitchen so we see it every day.

How did Ashley start her company? By starting it ;)

There are no shortcuts at a startup. It’s consistent hard work over time.

Here’s the thing though…

Having internal clarity on:

• what the work is
• who is doing it
• when it will be done

...can 5x ¹ your company’s pace and effectiveness without changing anything else!

If you’ve ever said:

Me?!? I thought you were going to do it.

What came out of that awesome brainstorm session?

I feel like we have good meetings but nothing comes of it...

You need 3D:

• 📝 Do
• 🙋 DRI
• 📅 Date

The 3D Formula

Start here

After every meeting —formal or informal — ask a single question:

What are next steps?

1. **DO** Identify action items

• Be specific!
• Include numbers
• ✅ Send personal email to 10 customers for December user group

2. **DRI** Ask who will be the Directly Responsible Individual per item

• Also called “owner” or “point person”
• Only 1 DRI per item. 2 DRIs = no DRIs
• ✅ Send personal email to 10 customers for December user group (Kathryn)

3. **DATE** Ask DRI for due date

• Always add buffer
• No, really. It will take 2x longer than you think.
• ✅ Send personal email to 10 customers for December user group by Nov 15 (Kathryn)

Extra Credit

Pause. Reflect on your 3D list.

Think about overall company priorities.

• Are these action items important?
• Should DRIs prioritize this over other work?
• Do these dates make sense given other company timelines?

😊 YES → Proceed. Enjoy the progress and clarity!

🙁 NO → Scrap everything without hesitation. You may have wasted time with this meeting but don’t make it worse. Get back to important things!

3D Recap:

• 📝 Do
• 🙋 DRI
• 📅 Date

Quick, simple, game-changing.

If you’re an early stage startup that wants to go faster, try this alignment and clarity tip. Let me know how it goes or if you’re one of the magical startups already doing it!

‍

¹ Estimated. Could be 2x, 10x, 1000x. No time to collect official data when we implemented this at Rigor and Pardot. We were moving too fast 😉

Operations at a fast growing startup can be like walking into a messy closet. Lots of potential but in need of some organization. You’re not sure where to start and it can be overwhelming to a Type A closet neat freak (not that I would be one of those… ;) )

If your early stage startup feels like a messy closet right now, is that bad? No! It’s completely normal. In fact, I would say, it’s a great sign that you’re focused on the right things (customers and growth) early on. If you add detailed planning structure too early, you’ll kill creativity, speed, and focus.

At some point though, the paradigm flips and without more clarity and structure, creativity, speed, and focus will fall off.

Whether you’re an ops leader with a “messy closet” or a CEO ready to scale, here is a *real life* story of incremental improvements over time to create operational excellence.

Our first quarterly planning session at Rigor:

• Presentation from each department
• One page quarterly planning template
• Variety of presentation formats, goal types
• Informal coordination and review

8 quarters later:

• Annual planning process including budgeting
• Quarterly planning process aligned with annual planning
• Company vision and goals defined and communicated
• Department projects and metrics aligned to company goals
• SMART goal format with dates, numbers, specific targets
• One page quarterly planning template by department, approved by CEO
• Cross-departmental coordination and visibility on priorities and goal setting
• Coordinated presentations approved by CEO, shared at company offsite
• Uniform, branded powerpoint presentations
• Follow up feedback survey
• Departmental metrics consistency with goals and actuals
• Mid-quarter leadership review of goal progress
• Performance reviews align with company goals and values
• Company core values defined and used in hiring, performance, planning, decision making

Did we implement all of these changes in a single quarter? Nope. It would have been incredibly time intensive with little adoption and minimal long term value.

Instead, we picked 1-3 things to add or focus on each quarter.

First, it was consistency with metrics and setting SMART goals. Next quarter, we added a leadership review and alignment process. Then, it was viewer-friendly presentations instead of one page templates. After one quarter of presentations, we started doing dry runs and using beautiful, branded templates. By then, we had also redefined our company Core Values and incorporated those into planning, presentations, and performance.

How did we decide the “next thing” to add each quarter?

• Gather team feedback after each quarterly planning cycle
• Discuss with CEO
• Assess what didn’t go smoothly
• Analyze priorities and return-on-effort

Based on those inputs, we’d make a plan for what to improve next quarter. We’d also drop things that didn’t work and streamline areas that didn’t need hands-on management anymore.

Improvement Over Time

Like the famous British cycling team, we focused on consistent improvements over time which resulted in big gains in the long run. No single item was transformational but the operations snowball grew steadily.

Within a year, Rigor had developed strong operational muscle. Habits like using SMART goals started to happen automatically. Team members would remind each other about it and train new hires on it. We could focus on new habits like incorporating quarterly targets into daily and weekly cadences or project planning best practices. As familiarity with the process, expectations, and feedback loop grew, each subsequent improvement was easier to layer on.

This kind of operational rigor (see what I did there?) is always a team effort. It starts at the top with the CEO and depends on each team member adding their ideas, executing daily, and caring about improvement.

By building organically, incorporating feedback, and improving over time, a startup’s “messy closet” can become a highly-adopted, employee-driven system of operational excellence. It doesn’t happen overnight but, like most things at a startup, it will happen faster than you think!

The Pursuit of Happiness

One of my favorite things to read is happiness research. Except don’t call it “happiness”!

It’s satisfaction. Purpose. Enjoyment. Living a good life.

And it’s harder than it sounds.

It’s easy to fall into the trap of:

• Once I make x dollars, I’ll be happy.
• Once I lose y pounds, I’ll be happy.
• Once I get z job, I’ll be happy.

Then you achieve those things, and voila!

You feel...pretty much the same as before. Whomp whomp.  

So you set a new goal and get back on that hamster wheel to hit the next milestone. Because THEN, when you get to THAT ONE, for sure you’ll be happy.

And whaddya know? Same as before. Whompppp whompppp.  

So what really matters? What are the traps we fall into? What should we do in our lives to bring happiness and meaning? These are my favorite questions and here are five of my most recommended happiness resources (with a bonus item!).

5 Amazing Happiness Resources

1. The Science of Well-Being, free course by Yale Professor Dr. Laurie Santos

Laurie is amazing. She feels like a friend. You know, a friend who is one of the top professors and researchers in the world at one of the top schools in the world. That friend.

It’s accessible, it’s actionable, and it’s at your own pace.

I did this course in the midst of the pandemic (May 2020) and it:

• Gave me daily happiness habits to anchor around (sleep and exercise!)
• Got me started on a gratitude journal which I do daily and LOVE.
• Made me rethink my life (in case the pandemic wasn’t enough…)
• Led to life changes (new job) that I’m thrilled about!

Just in case my personal testimonial isn’t enough, 30,000+ people gave it an average rating of 4.9/5 stars. So, yeah. Not too shabby ;)

Extra Credit: Dr. Laurie also hosts The Happiness Lab podcast which is excellent.

2.  Blue Zones of Happiness, book by Dan Buettner

Dan studies the happiest people around the world to find the common denominators. I love that it’s research-based and global with specific suggestions.

For example, having sex weekly, eating lots of veggies, having a short commute, and owning a dog are common traits of the happiest people regardless of your culture or continent.

3. Why Some Men Pretend to Work 80 Hour Work Weeks, Harvard Business Review article by Erin Reid

One of my most-shared articles, Erin’s research is highly relevant to happiness. She studies workplace expectations, how men and women approach them differently, and highlights real life examples of how to work in demanding jobs but still make time for family, sleep, exercise, and the other things that drive life satisfaction.

If you feel like you “can’t” or want a “life hack” to find time to even think about happiness, read this one.

4. Mr. Money Mustache, blog by Pete Adeney aka Mr. Money Mustache

The name says “money” but it’s really about freedom and happiness. If money doesn’t buy happiness, what does? There’s lots of data and research within his blogs but some of his best are stories or hilarious rants:

• Lessons In Badassity From a Night in Houston
• Cure Yourself of Tiny Details Exaggeration Syndrome
• A Lifetime of Riches: Is it as Simple as a Few Habits?

5. Deep Work, a book by Cal Newport

Ground-breaking research by Mihaly Csikszentmihalyi showed that being in “flow” is one of our happiest states. How do you get there? Cal shares the research and gives specific strategies on how to do meaningful, “flow-state” work.

BONUS: Jessica’s ‘Daily Affirmation’, a YouTube video by 4-year old Jessica

No research, just the feels. If you need a happiness boost RIGHT MEOW, watch this video. Then stop and navigate away immediately.  Screen time and social media are no bueno for happiness!

Finding Happiness

Some of the major happiness themes that have stuck with me:

• Gratitude for what you have
• Sleep
• Exercise
• Eating healthy
• Spending time with people
• Spending time outside
• Having purpose and meaning
• Helping others
• Being part of a community

I’ve found that, like most good things, these strategies and activities are simple but not easy.

It’s a constant work in progress. In fact, I might even be on the happiness hamster wheel. If only I could get more sleep, then I will be happy… but for real this time!

What strategies have worked for you? Do you have favorite happiness resources?

CEOs, COOs, and operations leaders often ask, what is the best metric to assess operational success?

Operations roles can vary wildly, especially in high growth startups where company needs evolve quickly. The “right” metric differs based on company stage and role focus.

Four Operations Metric Ideas

1. Your company “North Star” metric
2. Everyone in every role should be measured on this!
3. Use this metric + another ops metric for internally-focused ops
4. Best for: ops role with heavy revenue or go-to-market focus
5. Employee Net Promoter Score (eNPS)
6. Two variations:
7. How likely are you to recommend this company as a place to work?
8. How likely are you to recommend our product or service?
9. Best for: ops role with heavy people operations or culture focus
10. Customer Net Promoter Score (NPS)
11. Very common, easy to find benchmarking and survey tools
12. Best for: ops role with heavy customer or product focus
13. Internal-version of Customer Effort Score (CES)
14. Two variations:
15. On a scale of ‘very easy’ to ‘very difficult’, how easy was it to <do task>?
16. On a scale of ‘very easy’ to ‘very difficult’, how easy is it to do meaningful work?
17. Best for: operations role with heavy internal efficiency and process focus

Real World Example

As COO at Rigor, our company “North Star” metric was Annual Recurring Revenue (ARR). My key operational metric was eNPS. We had other metrics and many operational initiatives but ARR and eNPS anchored our focus.

What Else?

What other metrics have you seen for operations leaders? What metrics-related resources have been helpful? Any recommendations or learnings on operations metrics at high growth companies?

What does a Chief Operating Officer do?

I get this question from early founders, CEOs wondering if they need one, polite friends trying to understand my job, even other COOs!

It’s clearly a valid question.

Why is the job of COO so murky?

1. The role looks different at every company.
2. COOs are often behind the scenes, letting others take center stage.

Nathan Bennett and Stephen A. Miles via Harvard Business Review put together one of the best summaries of the different flavors of COO: Second in Command: The Misunderstood Role of the Chief Operating Officer.

They detail the seven (yes, SEVEN - no wonder it’s hard to pin down!) types of COOs.

As COO of Rigor, I handled strategic operations, alignment, communication, facilities, people operations, and finance. My North Star metric was Employee Net Promoter Score.

At other companies, I’ve seen the COO add Go-To-Market, Product, Engineering, or Customer Success to their line up. At public companies, the COO often runs the company while the CEO focuses on vision, press, and investors. Sometimes, the COO is a co-founder or a CEO-in-training.

With all of these different “types” of COO, how should you think about the role?

The most important job of a COO is to complement the CEO.

No, that’s not “compliment” as in, a courteous remark that expresses admiration. That’s “complement” as in, something that completes something else in some way. (Reference for grammar nerds here.)

The COO is fundamentally a balancing role. It’s a leadership role that’s strong in areas where the CEO doesn’t have interest, time, or expertise. And this is different for every company since every CEO is unique.

So, what does a COO do?

• Complements the CEO
• Brings leadership expertise and execution to areas that need attention
• Customizes the role based on the CEO, team, industry, and business

Yes, the COO is often a strong “operator” - great at building repeatable programs that incorporate data, accountability, training, and tools in a structured way.

But the most important job of the COO is to see the needs of the CEO and the company and double down in those areas. It requires an honest, trusted relationship with the CEO and a deep understanding of people and business.

It’s a dynamic, challenging, and subtle role. When you get it right, great things happen.