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Updated: Jul 3, 2023

The notion of a 100-day plan is simple but effective. It’s essentially a plan of action to help guide you through the crucial first months of an executive-level or leadership position. Here, we’ve put together our own checklist to help you pave the way towards a long and fruitful career in a professional services leadership role from the outset.

Coming into a new role leading a professional services team right now is tricky; as economic forces are causing significant rethinking in how SaaS firms approach growth and profitability, boards and investors are looking to professional service function to deliver growth targets in a way that is scalable, efficient and economical. The most common question for a new head of professional services is ‘How can we maximize ARR without losing money?'

While Rome wasn’t built in a day, and you can’t be expected to achieve this overnight, there is a newly injected urgency into this request in the current business climate, giving you no time to waste.

This guide will help you make the most of your first 100 days in your new role featuring a roadmap for services that balances customer centricity, financial discipline and being people first.

Days 1 - 50: Stop, look, listen and learn

The first phase of our 100-day plan for your new professional services role is crucial. Your first 6-7 weeks in a new leadership position should be a time of assessment, understanding, and analysis.

Step one: Get to know your Customers

Although it's inevitable that you'll know your team well before your customers, we suggest that speaking to customers should happen alongside those internal conversations. This puts you in the best position to add value quickly, as you can build a more objective and customer-centric view of what challenges and opportunities exist in the professional service function, and know the right places to focus on.

You should be spending time listening to your customers from day one and get answers to the following:

  • What is working and what is not working for them in terms of your product and service offerings?

  • What is the business model for your customers? How do they generate revenue?

  • How do they describe the value of your solution to new hires / their boss?

  • What data do they generate from your product that helps them make decisions in their role?

Don’t just speak to your existing customers - look to speak to churned customers and to ICP businesses who are not customers for a more rounded picture of the situation.

“I'd say there are 5 key things to focus on in the first 30 days: 1: People - get to know each and their strengths and development areas. 2: Demand - understand your demand engine - what drives your PS business. Product lines, strategic or product services, what are your growth lines, what is declining, etc. 3: Operational Maturity - are governance processes in place, and are they effective, are there playbooks and delivery methodologies or do these need to be established, is resource management required, etc. 4: Customer Centricity - are the professional service team and their services delivering value to customers? Where is success visible and where needs to improve? Are there opportunities to do more? 5: Financials and KPIs - revenue, margin, utilization, CSAT - targets, actuals and where intervention may be required"

Jonathan Williamson

/ Group PS Director

Advanced Software

Step Two: Get to know your business

Next, you need to meet with the entire C-Suite to fully understand the business strategy and the mission statements of the overlapping departments, with a particular focus on:

  • Understanding the growth strategy from the CEO and how professional services are enabling the strategy.

  • Unpack the cost base and financial targets in terms of profitability and margin. Meeting with the CFO to understand the drivers (key cost input being people) and the levers to pull from a revenue and pricing perspective.

  • Speaking to the leader of the Pre-Sales/Sales engineering team to understand their role and how it currently dovetails with PS and CS in the overall sales process. When and how does PS engage during the sales cycle?

  • Reviewing the sales process with sales leadership and account executives to understand what the methodology and where professional adds value in the sales process, as well as understanding conversion rates and services attachment rates. It will also be helpful to understand AE comp plans and how they are incentivized (or not) on PS.

  • Speaking to the head of channel partners / alliances to understand the ecosystem and relationships with partners - particularly if you have partners delivering on your behalf.

  • Meeting with the Chief Customer Officer who increasingly owns the whole post-sale organization including services, CS and Support.

  • Your VP of Customer Success will be one of your key partners for collaboration, and getting to understand how these two teams partner together and what those transitions look like is key.

The first 100 days of a new role as a services leader are different from other roles - we are often trying to rebuild a plane in flight rather than on the ground. This puts a premium on spending time with the team, with peers across the organization, and - most importantly - customers, to understand what value means to them. TEAM - Always be Closing....recruiting. A services organization's lifeblood is amazing teammates and leadership team. Whether recruiting new teammates to the company or simply the existing team to your methodology/charter/mentality, getting the right people in the right seats is priority 1. PEERS - Services in a SaaS company has natural allies (Solution consultants, often CS) and some natural tension (Sales at times.) Learning how the sales team is compensated, what CS experiences have been with customers transitioned from your team, how finance does rev rec, what types of repetitive tickets support is seeing helps build empathy and positions you to be an ally in winning the market. CUSTOMERS - The best intel and strategy you will get in the first 100 days are customers you are actively working with or have recently finished. "Perception is reality" and the ability to talk live to customers, review CSAT/NPS scores, and anything to get into their perspective makes all the difference."

Peter Wride

/ SVP Professional Services


Step Three: Get to know your team

From here, your focus should move to more internal considerations, by meeting and consulting internally.

Before speaking to the team, it’s valuable to have knowledge of the organizational structure of the team and its design, and what a typical team looks like for an implementation, as well as understanding what the current career path looks like in the professional services team.

You will want to now turn to your team and continue to listen, in order to understand:

  • What are their goals?

  • What do they like and dislike about their role?

  • Review incentives for the services team. Are they measured on launch times, utilization, implementation CSAT - do these incentives align with your mission for services?

  • Ask for their understanding of the operating professional service model and see where outlines differ throughout the team.

  • Where do they see areas of improvement in the PS Organization?

  • What are the formal goals / KPI's / OKR's of your employees?

  • Are they aligned with the goals of your customers?

Hands together teamwork

Step Four: Get to know your Operation

You also need to have a firm idea of the operational model that the team is working towards by the end of the second month:

  • Take part in the process of how information is passed between sales, PS and CS to look for areas where the teams are aligned well, and any points of failure in handovers.

  • Understand and observe the delivery process at its various stages in your existing project portfolio to get a picture of the end-to-end process as is.

  • Learn how the customer support function operates and co-operates with PS.

  • Understand the roles and responsibilities you need, taking into account your operating model.

  • Understand how you are performing on the key metrics for service delivery. These include operational metrics (Utilization rates and implementation times), Customer-centric metrics (NRR, TTV, CSAT) and financial metrics (Revenues and Margins) - we recommend using our Professional Services KPIs blog to know what you should be tracking and how to find it.

"The other point I would make is that you need to understand your professional service team's purpose within an organization - are they there as a profit generating arm (drive for high margin and high CSAT), are they there to enable customer acquisition (cost center, or low or no margin, with focus on on-boarding customers, TTV etc.) or are they balanced in between. Knowing this will determine where focus needs to be with respect to any change or improvement initiatives"

Jonathan Williamson

/ Group PS Director

Advanced Software

If change is needed, you will need to evaluate the appetite and aptitude for change within the department. If the department seems resistant to change, you need to decide where you can change attitudes to make them more open to doing so - and where intransigence may need stronger changes.

Throughout this first phase of your 100-day plan, you will uncover issues or challenges that can be rectified and improved within the department. In order to make those improvements, you should have a clear understanding of what a successful professional services model will look like, to act as a north star for your plans.

This plan must work not just for the PS function as it exists today, but for what the department will need to deliver on according to the company's growth plans - futureproofing your service delivery is vital.

Days 51-100: Hatching a plan

Once you’ve passed the first 50 days in your new professional service leadership role, you can move on to the second phase of the 100-day plan. You can start to distill what you’ve learned so far into an assessment of the current status of the department, which you can then evangelize throughout the team, and begin to build a plan on how you will take things forward and the changes that are needed.

Below, we’ve outlined the key process you’ll need to go through in order to achieve this, as well as the questions you should be asking:

  • Start developing your plan.

- Use a framework to control how this plan is communicated effectively - we recommend our anatomy of a world-class PS function as a 12-point plan to start.

- What additional resources will you need?

- What things currently in place will need the biggest changes?

- What could be removed entirely, if anything?

- Ensure these plans are SMART (Specific, Measurable, Achievable, Relevant, and Time-Bound).

  • Your strategic priorities should start to be established by now. You should have your priorities mapped out. Again, you don’t need A-Z, focus on A-C at this point, you should have completed enough evaluation to know the strategic priorities for change, and have them mapped out in a roughly chronological order.

  • Your next place to gather information is in numbers - by ensuring that you gather the metrics that matter to your business - we recommend tracking the <twenty modern metrics every professional service leader should be tracking> to get an objective understanding of what is happening - remember that any numbers that you can’t obtain because the right things aren’t being collected, tells a story in itself.

  • Make sure you understand as a priority any deficits being created by professional services currently - our PS overrun calculator will help with this.

  • You should start to be thinking about locking up any internal support you might need (the buy-in). You will want to create a shared sense of ownership around your initiative(s).

  • Communication should also take hold during this phase, both formal and informal.

  • With any change, there comes the desired outcomes.

  • Remember, this isn’t a one-time exercise, you should already be thinking about regularly reviewing your process to insure it doesn’t lose momentum and has a real chance of adoption.

If you follow all of the steps in this plan, you will come to the end of your 100 days with an objective assessment of the professional service function from the point of view of your customers, leadership and within the team, and have used this to formulate a roadmap going forward to create a team that will help the business succeed in it’s strategic goals.


How Precursive can help...

At Precursive, our professional services automation software, or PSA software, helps service-based businesses better manage their operations by automating a wide range of business-related tasks, from project management and resource planning to time tracking and invoicing.

If you would like to find out more about how Precursive can help you increase your business's operational efficiency, get in touch

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