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Head of Sales

HelcimCalgary, Alberta, CanadaHybrid, Onsite

ABOUT HELCIM


Helcim was founded with a mission at heart: to be the world’s most loved payment system. We believe that by offering small businesses in North America a decidedly human payment solution where it is easier to sign up and use while being transparent and affordable, we can empower them to grow and prosper. Simply put, helping small businesses thrive is at the very core of our business model, and we think that’s a great way to do business.From the very start, we knew that we wanted to be different from every payment processor out there.

We want the merchants we serve to feel supported and see us as a trusted partner rather than simply just another “cost of doing business.” We are relentless in our pursuit to provide a radically transparent and honest payments solution that flat out saves business owners money, all while treating them like human beings.THE POSITIONAs Head of Sales, you will have the exciting opportunity to build and scale Helcim’s outbound sales function while also optimizing our inbound sales team. This is a critical leadership role that requires both strategic oversight and hands-on execution to drive revenue growth.You will be responsible for launching and managing a high-performance outbound sales team (cold-calling, telemarketing, and feet-on-the-street sales) while also enhancing the inbound sales experience to maximize conversion from interested merchants.

At the same time, you’ll shape a sales culture that aligns with Helcim’s core values—no high-pressure tactics, no hidden fees, just great service.  Our approach to sales is rooted in transparency and building genuine relationships.  We don’t use high-pressure tactics, instead we empower merchants with the knowledge they need to make informed decisions.  This means fostering a team that prioritizes trust and genuine customer care.

Here are the things you’ll own day-to-day:Outbound Sales (New Business Development)


  • Build & Lead an Outbound Sales Team – Recruit, train, and manage a team of SDRs focused on cold outreach, telemarketing, and in-person sales efforts.
  • Develop Outbound Playbooks – Define sales strategies, scripts, and outreach cadences that drive engagement and conversion.
  • Leverage AI & Automation – Implement AI-powered sales tools to enhance SDR productivity, personalize outreach, and scale prospecting efforts.

Inbound Sales (Conversion Optimization)


  • Manage & Optimize the Inbound Sales Team – Lead the team responsible for handling inbound leads, ensuring high-quality responses and maximizing conversion rates.
  • Refine Lead Qualification & Sales Processes – Ensure an efficient system for prioritizing inbound inquiries, following up with potential merchants, and improving conversion rates through effective ‘Speed to Lead’ best practice.
  • Collaborate with Marketing – Work closely with marketing to optimize lead handoff, refine messaging, and enhance the overall customer acquisition funnel.

Sales Strategy & Leadership


  • Create a High-Performance, Values-Driven Culture – Build a results-oriented sales culture that prioritizes integrity, transparency, and customer service.
  • Optimize Sales Systems & Workflows – Implement and refine CRM processes, call tracking, and sales automation tools to streamline operations and improve efficiency.
  • Data-Driven Decision Making – Use key sales metrics to evaluate team performance, identify bottlenecks, and drive continuous improvement.
  • Foster Cross-Team Collaboration – Work with marketing, product, and customer support to ensure a seamless merchant experience from first contact to onboarding.

A SUCCESSFUL CANDIDATE WILL HAVE:

  • Proven experience building and scaling both outbound and inbound sales teams.
  • Sales experience in the B2B SMB market. Payment experience is a bonus.
  • Strong leadership skills with a track record of building high-performance, engaged teams, and the ability to inspire a team to sell with integrity.
  • Experience in sales operations, CRM optimization, territory planning and process automation.
  • Proficiency in AI-powered sales tools and automation for outbound prospecting and lead management.
  • Passion for helping small businesses succeed and a commitment to ethical sales practices.
  • Data-driven mindset with a focus on key sales metrics and continuous improvement.

HELCIM CULTURE IS; 

Being builders: We build things ourselves and we build them well. We use technology and our creativity to overcome challenges that would seem beyond the capability of a company our size. We improve what is already there, invent our way out of problems and we never stop dreaming of better.

Choosing the harder path: We believe that the right decisions are usually the harder ones, so we embrace the challenge and endure when others quit. We choose what is difficult because it is more rewarding in the long-term, and makes us resilient, so that we not only survive but thrive.Creating trust: We earn trust by striving to be our best selves every day and by lifting those around us. We recognize that trust is hard to earn, easy to lose and is tested continuously over time, so we make trust our way of life.Contributing to a company of many: We are stronger because of our collective passion, diversity, and fellowship.

We believe only great teams can accomplish great things, and we ask the very best of each other. Together we create our own future.WORKING AT HELCIM  

Joining Helcim means joining a fast-growing company where we have found coming together makes us a strong company.  We have a drive to achieve big things which creates amazing opportunities for everyone willing to work hard and contribute to that growth - opportunities for faster career growth, for more learning, more impact, and accelerated experience - all while surrounding yourself with incredible people working on interesting problems and delivering great results.

Here are some of the reasons we attract such great people:

The Way of the Helcim:  At Helcim, we build a team of engaged, caring and intelligent people.  In return we provide an environment where you can be excited to come to work each day and tackle these challenges with an amazing team.  Learn more about Helcim’s unique culture and environment in our culture book The Way of the Helcim.

Health and dental benefits: Through our Group Benefits, you’ll get access to dental benefits, extended healthcare benefits for drugs, vision, paramedical coverage (e.g. massage therapists, dieticians, mental health professionals), counseling, health service navigation, life insurance, critical illness and disability insurance, and more. All of these benefits come into effect on Day 1 of employment!Dedicated Health Spending Account (“HSA”): An additional budget available for you to spend on health-related expenses (e.g.

eyeglasses, therapy).Maternity  and Parental Leave: To help launch our team members into this phase of family life we have some additional benefits in place including salary top for the birthing parents and a bonding break for non-birthing parents.

Stock Options: Stock options enable our team to purchase Helcim shares at a future date at a specified price. Every team member, not just people leaders and executives receive equity (aka ownership in the company).Vacation Time: All team members get paid vacation time and a company break in December so they can recharge when they need it. 

Flexible work location: Work and life happens at different times and places. This is why our team enjoys the flexibility of hybrid work and flexibility around hours of work, so we can all do our best work. Our hybrid work schedule offers flexibility to work from home on Tuesdays and Thursdays. Furthermore, our core hours give team members flexibility to manage other parts of their lives.

Training: Helcim will cover 50% of the applicable training costs of up to $500 per year.

Life at Helcim

Thrive Here & What We ValueBeing builders: We build things ourselves and we use technology and our creativity to overcome challenges that would seem beyond the capability of a company our size. | Choosing the harder path: We believe that the right decisions are usually the harder ones, so we embrace the challenge and endure when others quit. | Creating trust: We earn trust by striving to be our best selves every day and by lifting those around us. | Contributing to a company of many: We are stronger because of our collective passion, diversity, and fellowship. We believe only great teams can accomplish great things, and we ask the very best of each other. Together we create our own future.</s> | Being builders: We build things ourselves and we build them well. | Fast-paced and high-demand company | Emphasis on developing team members to build them into well-rounded professionals | Collaborative environment with cross-functional teams | Flexible work location and hours | Access to health and dental benefits, dedicated Health Spending Account, maternity and parental leave, stock options, vacation time, and training opportunities.</s> | Being builders: Helcim believes in building things themselves and using technology to overcome challenges. | Choosing the harder path: Helcim embraces challenging decisions that are more rewarding in the long-term. | Creating trust: Helcim strives to earn trust by striving to be their best selves every day and lifting those around them. | Contributing to a company of many: Helcim believes only great teams can accomplish great things, and they ask for the very best from each other.</s> | Being Builders: We Build Things Themselves and We Build Them Well. | Contributing to a Company of Many: We are Stronger Because of Our Collective Passion, Diversity, and Fellowship.</s> | Creating trust: We earn trust by striving to be our best selves every day and by lifting those around us. We recognize that trust is hard to earn, easy to lose and is tested continuously over time, so we make trust our way of life. | Being builders: Helcim builds things themselves and uses technology and creativity to overcome challenges that would seem beyond the capability of a company their size. | Choosing the harder path: Helcim believes that the right decisions are usually the harder ones, so they embrace the challenge and endure when others quit. | Creating trust: Helcim earns trust by striving to be their best selves every day and by lifting those around them. They recognize that trust is hard to earn, easy to lose, and is tested continuously over time, so they make trust their way of life. | Contributing to a company of many: Helcim believes only great teams can accomplish great things, and they ask the very best of each other. Together, they create their own future.</s> | Being builders: We build things ourselves and we use technology to overcome challenges. | Contributing to a company of many: We believe only great teams can accomplish great things, and we ask the very best of each other. Together we create our own future.</s>
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