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First 100 Days: The VP Operator Playbook

The first 100 days of a new operator role at the VP or Director level are crucial. A three-time former Chief of Staff shares the ultimate VP operator playbook.

The first 100 days of a new operator role at the VP or Director level are crucial. Getting these first three months right sets the stage for team productivity, process efficiency, and faster learning.

However, many operators fail to get this period right. Without the proper context, support, tools, and mindset, they spend their first 100 days (and each subsequent one) putting out fires that could’ve been avoided with a bit of planning.

At FreeAgent CRM, we believe that B2B businesses benefit from proactive planning. We invited Carmeanna Eberly, Director of Operations at Refine Labs, to share her secrets. 

Carmeanna is a three-time former chief of staff and now runs operations at one of the foremost B2B demand generation agencies.

Carmeanna shares her playbook for VP and Director-level operators, gives plenty of examples from her time in the trenches, and offers valuable insights for those who plan on becoming the operational glue in their new companies.

What’s the difference between a Chief of Staff and a VP of Operations?

The VP Ops role and Chief of Staff role might sound similar in scope, but there are subtle differences worth noting.

Chief of Staff: Typically a generalist that touches every aspect of a company, or a technically specific role confined to one function or department within the company.

A generalist Chief of Staff might handle strategic operations, admin teams, events, internal communications, and assist with quarterly planning. 

Like a Swiss army knife, their mandate cuts across several parts of the organization, giving them the power and insight to influence decisions.

"When the executive team has its quarterly planning, they turn to you for guidance. How do we facilitate and implement it? How do we deal with change management?"

Meanwhile, a specialist Chief of Staff for a CTO might be well-versed in the operational needs of the engineering or technical teams, doing a more defined version of what a generalist Chief of Staff would do.

definition: chief of staff

VP level operator: Lays the foundations of each department within a company and helps subsequent leaders build on top of that infrastructure.

For example, a VP of Ops might build out the HR department and oversee hiring, onboarding, benefits allocation, payroll, and employee management.

After a few months of building out the function, they might recommend a new leader from within or outside the company to run that department.

They’d then work with that new leader to ramp up hiring, improve onboarding, manage vendors, and grow the company culture.

The result, says Carmeanna, is that VP-level operators end up consulting for and auditing other departments.

definition: vp operations

"I do a ton of consulting with other departments, so they understand the history of what we had in place, why we had it, and how to get us to the next level."

How should either of these two high-level operators navigate their first 100 days? We advise watching the full video above for all the insights – but if you’re pressed for time, here’s the high-level summary:

  1. Align with your leadership team on vision and direction
  2. Gather historical context to inform future strategy
  3. Set priorities and use automation, delegation, or deletion to preserve bandwidth
  4. Understand the company’s planning cadence and use that for forecasting
  5. Know who’s accountable for reporting and which metrics to use
  6. Create psychological safety, champion your team’s needs, and lead with empathy

Let’s dive into the VP Operator Playbook and unpack those points separately.

#1 Align with your leadership team on vision and direction

Before taking on a high-level operator role, it’s important to align with the team’s leadership on the vision and direction the company will take. 

Backing the wrong leadership team or wrong approach to growth can lead to operational failure, team rifts, and career frustration.

"At a previous startup, I had a terrible experience with a CEO I supported. It taught me a lot about what to look for in an executive team and the kind of qualities I can back with my best work."

It’s difficult to fully assess who you’re getting into bed with at the interview stage because everyone is putting on their best behavior.

However, there are ways to gain insights into your future operational partners. For example:

  1. Do their views and vision align with where the market is going?
  2. Do their team metrics regarding hiring, retention, and growth match their operational needs?
  3. Does the management team have a positive reputation among their peers?

Answering these questions early on can save you a lot of frustration and misdirection.

Align with company leadership expectations

#2 Gather historical context to inform future strategy

Strategy determines the future state of the company — but mapping out the future without understanding the past is a recipe for disaster. 

As a new high-level operator, you want to familiarize yourself with the company’s history, challenges, products, stakeholders, previous solutions, and results. 

This gets you up to speed so you can plug into — and eventually influence — the company’s trajectory.

“A lot of these roles are expected to provide value quickly, which can be overwhelming for somebody who's brand new and lacks context. Prioritizing historical context is a great move.”

Gathering context helps you avoid suggesting solutions the company has previously tried and failed at. This saves you precious time and resources.

Beyond historical context, new Ops leaders need to assess the company’s direction to determine its viability. 

For example, does the product roadmap look realistic? Could you implement the desired additions or improvements given current constraints?

Even better, says Carmeanna, companies should document all this into an operating playbook that everyone can access. This aligns everyone on the business’s processes and potential gaps.

Document processes into an operating playbook

#3 Set priorities and use automation, delegation, or deletion to preserve bandwidth

With context in hand, a strategy in place, and goals to reach, operators can prioritize which goals to tackle first.

Ops leaders touch every aspect of the company, but their time and bandwidth are finite. This is where automation, delegation, and deletion come in.

As an Ops leader, you’ll juggle a combination of glass and rubber balls. You can’t drop the glass balls — or else they’ll shatter and stall progress. 

You can safely drop the rubber balls for later pick-up, throw them to someone else to handle, or ignore them completely.

Free up your bandwidth

Some tasks may be ripe for automation, requiring minimal time and oversight. Managing leave days, for example, can be automated, as can expense management for purchases under a certain threshold.

You can also automate project updates, customer communications, and marketing campaigns through tools like CRM software and marketing automation platforms.

“There's only so much a person can do. If you know your workload will soon balloon, ask for a resource. Hire a firm to come in and help or bring in someone part-time. Just get ahead of your needs sooner.”

Other tasks can and should be delegated to others within the company. This leaves you accountable for progress but gives them ownership.

However, setting priorities is not just choosing what to tackle and what to drop — it’s also about communicating these priorities to everyone involved.

This means setting up a meeting cadence with upper management, departmental peers, and direct reports to build rapport quickly, understand their communication and working styles, and align on expectations.

“You folks don't know each other yet, but you’ve suddenly acquired responsibility, autonomy, influence, and accountability. The impact of establishing trusted relationships with your leadership team snowballs.”

Set up meeting cadences

#4 Understand the company’s planning cadence and use that for forecasting

It’s also vital for new Ops leaders to understand the planning cadence of the company. 

Whether monthly, quarterly, or bi-annually, knowing how often plans and priorities get reviewed and introduced helps you with timelines, forecasting, and reporting.

Your departmental budget will determine what you’re able to do and what resources you can bring on. 

Forecasting helps you be more proactive and less reactive in planning hiring, marketing, and sales initiatives.

“We are constantly reviewing our headcount and doing forecasting exercises to understand what we need. You never want headcount to affect new customer acquisition.“

Forecasting helps you be more proactive

#5 Know who’s accountable for reporting and which metrics to use

As a VP or Director of operations, a huge component of your job is auditing, tweaking, and refreshing internal processes. This requires visibility through timely reports.

Reporting is usually a pain point for executive teams, which prompts them to bring on an operator in the first place. 

Your job is to figure out what needs to be reported, what metrics to use, and how to turn that data into insights that power each department you work with.

“Understand the reporting frameworks your company has been using so far. Are you using OKRs? Are you working on a project-by-project basis? Are you doing these projects in sprints?”

However, ownership of reporting must be clearly defined. Having too many owners may result in disparate figures and haphazard strategies. 

Ownership and accountability go hand-in-hand, and operational leaders should know who they’re accountable to and who’s accountable to them.

“As a director of operations, I might report directly to the COO, but I'm accountable to the CFO for a departmental budget. As an Ops manager, you are accountable to your line manager, but you're also accountable to your direct reports for developing them and ensuring their work quality reflects expectations.”

Reporting is key

#6 Create psychological safety, champion your team’s needs, and lead with empathy

As a new Ops leader, you might have joined the company because of their leadership team, company trajectory, market growth, diversity, or challenges. Most likely, it was a combination of one or more of the above elements.

As you ramp up hiring, include those elements in your hiring strategy and employer branding to attract the same high caliber of people.

“When I was interviewing at Refine Labs, the CEO and COO kept posting about their investment in employees. Posting that on LinkedIn to thousands of followers creates a public web of accountability, which I thought was amazing. That's the kind of place I feel psychologically safe in helping to build.”

Psychological safety also involves creating space for failure, learning, growth, and integration from non-traditional backgrounds. 

Job descriptions that over-emphasize winning and success, for example, may imply that failure isn’t tolerated or that there’s no room for experimentation.

Similarly, job ads that require specific schooling or career backgrounds may exclude great candidates that graduated from a different school or started their careers in a different field.

“You don't want to miss out on cool candidates because your job descriptions are not equitable or welcoming.”

Create psychological safety

Carmeanna was employee #12 at Refine Labs back in November 2020. The agency now boasts 112 employees and aims to hit 250 employees by the end of 2022. 

That kind of growth brings new challenges, and operators at scale-ups need to bolster a company’s foundations to accommodate all those new faces, spaces, and working paces.

“Many initial startup tools and strategies used are bandaid solutions that help you get by. You'll survive with them, but they won’t grow with you past 15 to 25 employees.”

And where there are humans, there is friction. Dealing with difficult personalities is part of the job, and the correct approach is to lead with empathy.

This means understanding where the other person is coming from, what their role entails, and what challenges they may be facing — before casting judgment or taking action.

“Often, people don't know how to communicate or express themselves. It could be a language barrier, or feeling overwhelmed and lacking the skillset to express their stress and frustrations.”

In the end, you are on your team’s side as an operational leader. Your job is to champion their needs, boost their morale, and remove blockers from their way. This incentivizes your team to bring their best selves to work.

Lead with empathy

Be the glue

As an Ops leader, you’re the glue of the company. Your work serves to bring together disparate systems, coach people to produce their best work, influence stakeholders to align with the vision, and champion the needs of your direct reports.

People come to you for guidance on building on top of your set foundations. You’re a cross-functional member of the company, called on to get approvals, build plans, prioritize goals, and improve people and processes.

“Make yourself known, meet people, get to know them, and establish trust, authority, and autonomy. It goes a long way.”

Gluing a new workforce requires strong communication. Dive into our guide to internal communication to master this crucial aspect of your new role.

Mo Shehu

Mo Shehu

Mohammed Shehu, Ph.D. writes on marketing, content, and tech for B2B brands. You can find him online @shehuphd everywhere.

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