Bolster
For CEOs

5 Crucial End-of-Year Projects (And How to Outsource Them)

It may be peak vacation season outside, but CEOs know that the dog days of summer precede a jam-packed fall season full of new business opportunities and the race to the finish by the end of the year. Over the next couple of weeks, take stock of some of the business essentials and make sure you have a plan in place to conduct these important “health checks” across your organization.

At Bolster, we’re seeing a growing trend of CEOs looking to optimize their internal team’s time and priorities as much as possible, which often involves carving out key projects to outsource to on-demand leaders. Below, we’ve identified five of the most common end-of-year projects, and how to outsource them so you can keep things moving internally as fast as possible.

1. Establish a performance management framework

What is it: Leading up to annual bonus season and reviews, many CEOs and company leaders use this time of year to revisit their company-wide expectations around performance management, including evaluating current processes, designing feedback systems and training employees and managers on processes and practices.

You might need this if…

  • You’re hearing feedback from colleagues that expectations and growth opportunities are unclear
  • You are seeing uneven performance across the organization
  • You’ve recently added in a layer of mid-level management
  • You’ve grown your employee population substantially in the past year

How to outsource it: Hire a former Chief HR Officer as a consultant to evaluate current performance systems, identify gaps, provide recommendations for a framework that aligns with your culture, and implement the agreed-upon framework.

Estimated project time / scope: 1-2 months for plan design, 1-2 months for implementation

2. Update your financial models with cross-functional feedback

What is it: A crucial best practice at any growth stage, CEOs and CFOs dedicate some time on an annual basis to revisit the financial models of the business incorporating cross-functional feedback from all departments to rework the model for the following year.

You might need this if…

  • Your sales and marketing orgs are building a new plan for the following year, or engineering and product have key product releases coming up
  • You’re prepping for a fundraising or liquidity event in the next 6-12 months
  • Your business model, revenue projections, or cost structure has changed meaningfully in the past year

How to outsource it: An on-demand CFO can temporarily embed themselves in your organization, conduct a stakeholder analysis, and assist with your annual financial models; many CEOs at the earliest stages find it helpful to have an external set of eyes on their finances.

Estimated project time / scope: 1-2 months

3. Run an engineering team & emerging technology audit

What is it: Engineering and product leaders find it helpful to routinely look around the broader ecosystem for new tools, implementations, or technology that might optimize business performance or operations. CTOs also recommend conducting an annual “process analysis” to review engineering and product team processes internally.

You might need this if…

  • Your product or engineering team has been using the same tools, technology, and internal processes for a year or more without a change
  • You’ve started a list of other technology or systems to evaluate but haven’t had time to explore or conduct a comparative analysis
  • You’ve noticed a broader trend among peers in your space about migrating certain services to new providers
  • You’re starting to notice organizational growing pains with regard to team communication and management and may need to reevaluate your workflows

How to outsource it: Technology & team audits are easy projects to outsource because your on-demand CTO needs only minimal involvement in your own code base; the right person can conduct a comprehensive analysis, interview the relevant internal stakeholders, and help you focus your team’s attention on the highest priority opportunities.

Estimated project time / scope: 1-2 months

4. Rework your sales commission plan structure

What is it: With business models and revenue streams rapidly changing at high-growth businesses, it’s important for CFOs and CROs to keep an eye toward the bonus and commission systems that motivate, incentivize, and reward sales team members and team leads and perhaps most importantly have clear alignment between the team performance and the company performance.

Consider reworking if…

  • You expect your business model to pick up additional revenue streams over the next 6 months
  • You’ve recently brought on a layer of sales team leads or sales executives and need to build additional structure into your commission plan
  • You’re planning to launch into new geographic markets, industry verticals, or business stages
  • Want to ensure alignment with a Monte Carlo analysis

How to outsource it: A project-based CFO or CRO can help you quickly assess your current revenue streams and projections to make recommendations on how to best incentivize your sales organization to drive toward the right business outcomes for the next 1-2 years.

Estimated project time / scope: 1-2 months

5. Revisit your healthcare benefits design

What is it: With open enrollment season quickly approaching, the summer and fall is naturally the time of year when many CEOs and HR leaders revisit their employee benefits plan design.

You might need this if…

  • You’re receiving feedback from employees that your benefits are not competitive in the marketplace and you’d like to explore new ways to leverage employee benefits as a recruiting tool
  • You aren’t sure if your benefits plan will scale with your growth
  • You’ve ready to move off a PEO or take benefits plan administration in house

How to outsource it: An experienced HR professional with deep expertise in benefits plan administration and design can help you map out the landscape of healthcare options, manage the operational overhead, and oversee the internal communications of a plan transition.

Estimated project time / scope: 2-3 months

- Bethany Crystal, August 17, 2021