What it’s really like to be an executive at a startup – and how it’s different from being a director or manager

Business Impact: What it’s really like to be an executive at a startup – and how it’s different from being a director or manager
Business Impact: What it’s really like to be an executive at a startup – and how it’s different from being a director or manager

Prior to becoming a startup executive, my view into the role was limited. I saw how the ‘executives’ behaved in our one-on-one meetings and while presenting to our entire company during all-hands meetings. I noticed how they emailed, messaged, and comported themselves at the office. I observed how they spoke in our companies’ all-hands and how they behaved at holiday parties.

I watched them, as most startup employees do their leaders. (If you’re reading this, know that people are paying attention to your behaviour.) But my view wasn’t close to the full picture of what their roles demanded. At various companies I’d worked for, many of the executives’ calendars were fully booked in meetings so often I wondered how they got any work done. What were they doing during these blocks? Beyond their ‘busy-ness’, I wondered what that translated to in terms of what their jobs required on a day-to-day, weekly, or quarterly basis.

Inner workings of startup leadership are hard to see

Now that I’m an executive, I understand that the bulk of work done by an executive’s team is challenging to grasp as an individual contributor or even mid-level manager. While there’s been a movement to increase transparency across the startup ecosystem and more companies openly share their operating principles and salaries to their employees and even to the public, much of the inner workings of a startup leadership team are hard to see if you’re not a part of it.

‘The more senior you are, you execute less, and you have to be efficient with your time and need to empower your team to achieve your goals,’ says marketing executive Rachel Beisel. ‘You’re in a lot of meetings because you’re often the facilitator between departments and between employees in those departments.’

The reason that executives spend so much time in meetings is that decision-making is their most important responsibility. While startup leaders will always execute to some degree at earlier-stage companies (including the founders and CEO), their ability to strategise and decide is whythey exist at the company.

‘As a founder, I have decision fatigue,’ said AQUAOSO CEO and Co-Founder, Chris Peacock. ‘I expect my executives to constantly make good decisions in their areas, even in the absence of all of the data.’

Executives are charged with managing managers, meaning their direct reports generally have their own reports. This ‘skip level’ hierarchy requires executives to empower their reports to make good decisions and own theirareas.

The level of hands-on work you do as an executive will vary based on your startup’s stage and maturity. Early on in a startup, you’ll be spending more time on execution, doing things like shipping a new landing page, or editing copy, or creating financial models. These deliverables are a big part of how your success is measured early on. But as your company grows, you’ll need to delegate and manage other people who can do those things while you manage their productivity.

A week in the life of a startup executive

A sample startup executive’s schedule:

Daily

• Checking dashboards to view metrics and results measured against quarterly and/or yearly goals.

• Providing feedback to campaigns or other work products of teams within your team, usually at key milestones – early to verify direction (for example, this product roadmap change aligns to our strategy for the business/team) and ‘buy-off’ at final stages of delivery (yes, this press release has my seal of approval for publication, and my job is on the line if we screw it up).

• Cross-functional meetings with other executives or departments.

• Reading up on the latest news in your market or industry vertical.

• CEO syncs and department team meetings.

• Checking in on project management updates from your team on Slack, Asana, or another communication tool.

Weekly

• One-to-one with your direct reports; ensuring your reports and their reports are succeeding, and the team is tracking to Objectives and Key Results (OKR); troubleshooting any issues; and tracking their career goals.

• Weekly updates cross-functionally to other teams and your CEO.

• Measuring progress against OKRs.

• Feedback and/or signoff on key projects in your department.

Monthly

• One-to-ones with your direct reports; ensuring your reports and their reports are succeeding, and the team is tracking to OKRs; troubleshooting any issues.

• All-hands presentations to the entire company and/or business unit.

• Board updates.

• Updates to your CEO and/or cross-functional stakeholders.

Quarterly

• Reporting on a Quarterly Business Review (QBR) and/or Objectives and Key Results (OKRs).

• Evaluating strategic decisions weighing performance and/or new data.

• Board updates—deck, pre-read materials, and/or live presentation in a board meeting.

• Setting OKRs for the next quarter or half.

Annually

• Annual reviews and retrospectives, including reporting wins, failures, and what you’ve learned to your CEO, fellow executives, and the board.

• Annual planning, forecasting, headcount, and budgets.

• Financial models and planning – tracking CAC and LTV.

• Supporting fundraising efforts.

• Performance reviews for your teams and yourself (sometimes semi-annually).

Your daily, monthly, quarterly, and annual activities depend on the maturity of your department and company. Smaller startups may forgo annual planning and instead rely on quarterly planning cycles. You and your CEO may meet three times per week vs. once, so take the above with a grain of salt.

Other differences between non-executive and executive roles: accountability

Startup executives are accountable for delivering business results to company shareholders, including your co-founders, fellow executives, the board and investors (your founders’ bosses), and other employees. As an executive, you have the most ownership (which most likely includes equity) and accountability of anyone on your team. Unlike individual contributors or mid-level management, startup executives must build business strategies and execute them. Jennifer Rice, a leader at Pavilion,refers to the concept of building business opinions (vs. being an order-taker) as ‘having a theory of business’.

As a marketing executive, I am expected to form and communicate data-driven opinions on how to generate demand within target accounts to increase my startup’s market share and grow revenue. My CEO and cross-functional peers can help and my team will provide input, but, ultimately, I own and put my name on a plan. I need others to believe in the plan, but first I have to believe in it and champion it. When it succeeds or fails, I am the one who’s responsible. No one will hand these plans to us to go execute as startup leaders as they did when we were mid-level managers (although great ideas can and do come from anyone on the team). It’s on us to strategise and enable our teams to deliver results.

This is an edited extract from Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams by Sarah E Brown (Wiley, 2022).

Sarah E Brown is a mentor at the Techstars and Backstage Capital accelerators and the Founder of Flatirons Tech, a diversity- and inclusion-focused group from Boulder, Colorado in the US.

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