Sales - Head, Sales

Job Details

POSITION: Head, Sales
REPORTS INTO: Chief Executive Officer, Nancy Peterson
LOCATION: 49 Spadina Ave., Suite 200, Toronto, ON
STAFF: Four direct reports including Director of Business Development, Director of Training, and one Eastern and one Western Canada Sales Manager. Currently 15 indirect reports, with plans to grow to 50+ in the next 24 months.


Canadians spend over $70B annually on their homes - whether it’s major renovations, or small repairs and maintenance work. This journey often starts by finding the right contractor. HomeStars is the #1 website in Canada that helps homeowners with their home renovation needs. Every month, over half a million homeowners visit HomeStars to research and connect with the best-rated home professionals near them. Home Service Professionals advertise on HomeStars to tell their story, and grow their business with highly qualified connections. HomeStars has recently been acquired by HomeAdvisor, the #1 marketplace in the US for helping homeowners connect with the best home service providers. This creates new opportunities and unlimited resources take the HomeStars business to the next level.

HomeAdvisor is an operating business of IAC/InterActiveCorp (NASDAQ: IAC), a leading media and internet company. IAC owns some of the most recognized brands and products in the world, operating in over 200 countries, and include, Tinder,, Daily Beast, Vimeo and Investopedia amongst many others. IAC has over $3B USD in annual revenues and a market capitalization of $8B USD.


The Head of Sales provides leadership, direction and resource stewardship to the organization's sales and business development functions. As the organization’s senior-most sales leader, the Head of Sales is accountable for overall sales organization performance, the profitable achievement of sales organization goals, and for aligning sales objectives with the company’s business strategy. The sales leader reports to the Chief Executive Officer, Nancy Peterson.

Specific responsibilities include, but are not limited, to the following:

- Meets and exceeds team targets for profitable $ revenue, unit customer targets, and other key SaaS financial and business KPI’s. Achieves broader corporate objectives for revenue, profits, retention, ACV and other strategic goals.

- Aligns the sales organization’s objectives with HomeStars’ business strategy through active participation with the leadership team in corporate strategic planning, sales strategy development, bottom up forecasting, team resource planning and budgeting.

- Scaling a high performing team. As the sales leader it will be critical to build a strong team and sales culture. Like a strong sports team has been properly coached and developed, it can mean the difference between not quite qualifying for the playoffs and winning the cup. Working with our recruiting team and Director of Training, it will be critical to attract the right inside sales people on an ongoing basis, onboard them and grow the best sales culture. This could involve backfilling, helping close deals and working on key deals with them. Spotting issues before they blow up. Seeing opportunities ahead on the horizon. In general, making sure the 4 direct reports, and 15+ indirect reports work to their potential, and are our best brand ambassadors. This role will be expected to quadruple the number of players in the next two years.

- Effective sales organization design, including new roles and job descriptions, commission and compensation planning, sales channel design, training and people development. Establish and govern the sales organization's performance management system utilizing SalesForce reports and dashboards. This includes establishing sales organizational principles for managing performance, establishing and prioritizing critical performance measures for all sales jobs; overseeing the equitable allocation of organization objectives across all sales channels, markets, and personnel; and ensuring all key sales and sales management associates are held accountable for their assigned results. This is where the rubber hits the road - compensation matters. How can this be designed to motivate the best, to achieve their best?

- Building a clear sales process, pricing strategy with new product(s) - HomeStars will be launching a new product and looking to drive significant growth over the next 5 years. This role is a pivotal one to build sales processes, segment customers, and optimizing how best to work with the demand generation and marketing functions to grow the product portfolio. Activities to drive the supply of new service professionals will be coordinated with teams working on homeowner demand. A key focus area is learning and understanding how to maximize the % conversion of leads and revenue per lead. There will be a need to understand the customer journey and align this with the Customer Care division. Work closely with the VP Engineering & Product to ensure technology initiatives are implemented consistent with the firm’s technology strategy. Delivering effective product and process training will make or break the success of the product launch.

- Working with the HomeStars Leadership Team which includes functional peers in Marketing, Customer Care, Finance, Product and Engineer.


- University degree from an accredited institution. Master of Business Administration an asset.
- Minimum fifteen years of sales and sales management experience specifically in a SaaS and business-to-business sales environment.
- Has successfully grown high performing teams, demonstrating operational excellence
- Strong knowledge of SalesForce, Google Analytics and other analytical tools.

Ideally this candidate is already a leader in sales management and is interested in moving to a C-level position at HomeStars, as the team scales and significant growth is achieved.


HomeStars has a strong, winning culture that starts with our leadership team. Its foundational values are built on creating a trustworthy, respectful environment that gives people accountability and ownership to solve problems, and reward results. HomeStars’ mission of helping homeowners connect with the best home improvement professionals inspires their team to always try to do the right thing. HomeStars has made the Profit 500 list of Canada’s fastest growing companies five years running.

Perks of working at HomeStars
- Located at the heart of the downtown technology and garment district at Spadina and Front, HomeStars is in a historical 100+ year-old brick and beam building. The Company is growing fast and will be opening up an additional 2500 square feet space next door, with 35 additional desks to grow the inside sales team.
- Comprehensive benefits package from Great West Life. Their intent is a healthy and happy team.
- Annual three-day planning retreat in Muskoka for all staff across Canada.
- December break. The office is closed the week before New Year’s.
- Personal Growth. HomeStars provide employees with unique projects and ongoing constructive feedback to foster their career growth. Educational course fees are covered on an ad-hoc basis.
- Relaxed, open office environment to encourage collaboration. Frequent lunches are provided along with social events, and a games room with Ping Pong table, darts, and foosball.


If you are interested in exploring this opportunity, please contact:

Larry Chan
Rosenzweig & Company Inc.
(416) 646-3918 office
(647) 716-4846 mobile


Full Time

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