Staircase Ventures Advisor, Angelo Papatheodorou, on determination, focus, and building a powerful sales organization

March 3, 2024

The Advisor Series – Angelo Papatheodorou

Staircase Ventures has an outstanding team of advisors supporting our portfolio companies. In this blog series, we are introducing you to each of our advisors, sharing their stories, and highlighting some of their insights and advice on building startups.

Introducing Angelo Papatheodorou!

Angelo is the former Senior Vice President of Sales at PointClickCare. He joined the company in its earliest days and helped scale the company from a 3-person team to a powerhouse with over 2,000 employees and 160+ person sales team delivering $350 million in ARR. Angelo is an experienced sales leader and knows a thing or two about building and scaling startups.

In this post, we will dive into Angelo’s path to joining PointClickCare and share some of his advice on building scalable sales teams, including his thoughts on

  • Hiring and culture
  • Compensation and incentive structures
  • KPIs and forecasting
  • Transitioning from founder-led sales to a sales leader
  • Building a repeatable sales process

The Journey to PointClickCare

Angelo’s journey is a fascinating story of grit, determination, and resilience. He was born and raised on the shores of Lake Nipissing in North Bay, Ontario, spending his childhood and teenage years working for the family’s restaurant business. A desire for something more brought him to Toronto, hoping to build a career outside the confines of the hospitality industry. However, the first few years were nothing short of challenging. Angelo found himself navigating the streets of Mississauga, sleeping in his car or on friends’ couches and working odd jobs. While working at the Beer Store and pumping gas at a gas station (where he’d often park his car to sleep for the night), Angelo would chat with folks and pass out his resume, searching for a better opportunity.

Angelo was determined, and after many months, his resume found its way into the hands of a senior executive at Clearnet (now TELUS) in Scarborough. As fate would have it, Angelo landed the job at Clearnet, and his endeavour into technology began in the fall of 1996. The role was fairly simple; Angelo would answer new customer calls in order to assign new telephone numbers and activate cell phones.

Not long after starting at Clearnet, Angelo met Mike Wessinger in February 1997. Mike and his brother Dave had recently founded Wescom Solutions (now PointClickCare). Mike was looking for a sales rep and while Angelo’s sales experience of working in the beer store was not what Mike had envisioned for his first sales hire, as Angelo says, “I was all he could afford”. Angelo was hired as the first employee of the company. Despite his lack of sales expertise and familiarity with the long-term care industry, Angelo embraced the role with a keen desire to learn and grow, combined with unfailing grit and determination. Angelo led the sales function for 24 years, growing the team to over 160 people with over $350 million ARR. Today, PointClickCare is one of Canada’s most valuable privately held technology companies.

Angelo’s journey with PointClickCare was not without its challenges. There were many ups and downs. In the earliest years, Angelo often thought he would be fired due to weak sales. Nonetheless, he and the team persevered. A couple of years into the role, Angelo had the idea to invite 20-25 of their existing clients to ‘work the booth’ with them at a trade show. The plan was to have live client testimonials throughout the conference. The customers’ willingness to go to bat for them and the reception from potential new clients was overwhelming and it kickstarted a monumental moment for the company’s growth. It worked so well, they were signing up multiple new clients every single day for months following the event.

There were many lessons learned along the way in Angelo’s journey with PointClickCare and the following advice for startups is rooted in those experiences.

Hiring and Culture

Hiring the right people is one of the most important things your company can do. Angelo suggests the following:

  • Hire slow and fire fast. Take your time when hiring; it’s a significant investment and you want to ensure you hire the right people the first time.
  • Hire people smarter than you and surround yourself with good people.
  • If you’re early-stage, you don’t necessarily need to hire seasoned sales reps. What’s more important is that they’re hungry, driven, and learn quickly. Folks looking for large salaries and not incentive-based structures are often low sales performers.
  • Ensure all your hires are a good fit for the culture. Foster a positive and collaborative culture within the organization.
  • Analyze your top performers and find out what makes them successful. Look for those qualities in potential new hires. Consider using an assessment tool such as DiSC, Plum, or Birkman.
  • Use LinkedIn to find candidates with the right industry experience and reach out to them directly.
  • Ask people who have years of experience in hiring and managing sales teams to be involved in the interview process.

Compensation and Incentive Structures

Incentivizing a sales team effectively is crucial for driving motivation, productivity, and performance.  Angelo believes:

  • It is important to ensure that your sales reps are being paid according to industry rates, keeping in mind your company’s stage.
  • At the seed stage, it is best to use modest base salaries with highly incentivized commission plans. Companies may consider including equity and options-based incentives as well, although typically sales team members receive fewer options than people of their same level in other functional areas because they receive commission.
  • A general rule of thumb is that a sales rep’s quota should be 3x to 5x their total compensation (base salary + target commissions).
  • A sales rep’s quota should be challenging yet attainable.
  • Consider awarding smaller forms of performance-based compensation on a weekly, monthly, or quarterly basis.
  • Other forms of incentive-based compensation that founders or sales leaders should consider include Presidents’ Clubs, founders’ circle recognition, and annual awards. Implementing a bit of internal competition can go a long way.

KPIs and Forecasting

Setting clear objectives and tracking KPIs that are meaningful to the success of the business is crucial. Once a company has established product-market fit and a repeatable sales process, Angelo believes that your sales leader should be able to forecast sales within a 6-9% accuracy range for each quarter. To reach this accuracy, sales leaders should do the following:

  • Set KPI targets that you and the sales team are accountable for achieving.
  • Ensure everyone on the team understands the KPIs, how they are calculated, and how they impact the overall business.
  • Develop a list of KPIs that are most applicable to your business, but try to generally stick to the standard sales metrics:
    • Daily, Weekly, Monthly Sales Revenue
    • New Logo Sales
    • # of Upsells
    • Marketing Qualified Leads (MQLs) to Sales Qualified Leads (SQL) conversion rate
    • MQL Source
    • Win/Loss Ratio
    • Average Days Open in the Pipeline
    • Average Days to Close
    • Total Number of Leads
    • Number of Leads by Segment
    • Activity Metrics such as number of calls, emails, customer touchpoints
  • Learn from your customers and adjust the sales cycles stages in your CRM to align with the sales cycle of your business. The more you understand your client, the more accurate the pipeline analysis will be. Don’t be afraid to modify the template pipelines from CRM tools like Salesforce/HubSpot.
  • Over-inflated pipelines create noise and can be a distraction. Aspire to have a clean, predictable pipeline.

Transitioning from founder-led to a sales leader

Transitioning from founder-led sales to a sales leader is a crucial step in scaling your business. Many founders often struggle with this. Here is Angelo’s perspective and recommendations for success:

  • It takes time. Know that the transition is a slow process. Often a founder will be a “player-coach” for some time.
  • It is important to start giving up control to a sales leader relatively early on in the company’s lifetime, once a predictable sales process is in place.
  • Know your target market and ideal customer profile before making the transition.
  • Founders must determine the sales leadership needs, conduct the hiring, and define the roles and responsibilities.
  • Set clear goals, objectives and KPIs for the sales leader.

Building a repeatable sales process

Building a repeatable sales process is essential for driving consistency, efficiency, and scalability in your sales efforts. Here are some key factors to consider when building a repeatable sales process:

  • Reach out to other sales leaders and ask for their guidance. Your network and connections can go a long way. Don’t be afraid to ask for assistance.
  • Learn to say “no”. Sometimes founders or sales leaders will over-commit to close a sale. It is critical to make sure any opportunities you close will not be detrimental to the short- or long-term success of the company.
  • Understand your pricing and packaging. Generally, if you’re not getting any pricing objections from potential customers, you’re not capturing enough value and you should think about increasing your prices.
  • As the company grows, it is key to collaborate and align with marketing around product positioning and marketing materials.
  • Use the bowling pin strategy: focus on the ideal customer profile, win that market, and then move to the next segment. Don’t get stuck throwing darts at the board and trying to pivot into an area for which you are not fit.


From landing your first paying customer to hitting the $100 million ARR milestone (and beyond), building a repeatable, scalable sales process is paramount. Scaling a sales team is a complex journey.  Adopting Angelo’s advice on hiring, building a strong culture, determining ideal compensation structures, setting clear KPI targets, transitioning to a sales leader, and building a repeatable sales process will position your startup for ongoing success.

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