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Senior Account Executive, New Business (Mid-Market)

Build your career at a tech company solving a real-world problem: the tedious and manual process of responding to RFPs. Help us innovate in the proposal space—and grow your career in the process.

Loopio is a workplace that unleashes learning & growth opportunities for our Loopers. We provide autonomous, challenging work that allows each employee to master their craft. We attract and retain people who are naturally curious, have grit and are eager to grow and build their careers. At Loopio, we genuinely support each other, because true success comes from working as #oneteam.


At Loopio, our Sales team has a direct impact on our customers and prospects through connecting with Loopio’s award-winning RFP response software that will fuel their growth. We are growing our team with the addition of a Senior Account Executive for our Mid-Market segment (companies with up to 2,500 employee size).  This role is pivotal in revenue-generating at Loopio, and the team has a significant impact on our growth. 


The ideal candidate has a strong blend of strategic thinking, previous SaaS experience, and a self-starter attitude. You are a B2B SaaS Sales professional who is excited to sell to Sales, Security, and Proposal Management teams.  You are curious, know how to listen, and understand what prospects are really saying. You work with prospects to help solve their challenges and help them identify solutions to challenges they may not even know they have. 


You will have a direct impact on the growth of the sales organization and, more importantly, play a key role in the success of Loopio!

What You'll Be Doing

  • Play a key role in growing Loopio by driving forward sales opportunities within a defined market segment to generate new business revenue

  • Partner with our Sales Development team to prospect target accounts and with the expectation to self-source opportunities every quarter  

  • Navigate complex sales cycles with multiple buyers. 

  • Inspire prospective customers by delivering a world-class sales experience, providing demos of the Loopio platform, and navigating through the complete buying process

  • Deliver and negotiate sales proposals to prospective customers and work closely with senior leadership to close large opportunities

  • Build strong partnerships with your prospects and prepare them for success as customers with our Customer Experience team

  • Meet (and exceed) quarterly sales targets and consistently deliver accurate forecasts to sales management and Loopio leadership

  • Work closely with Loopio’s Product team to help evolve the Loopio Platform based on market trends and customer requirements

What You'll Bring to the Team

  • 5+ years of sales experience as an Account Executive or similar role, preferably in B2B SaaS, with a track record of proving success

  • Demonstrated experience  managing complex sales cycles with multiple stakeholders at Enterprise organizations from start to finish, with a strong ability to uncover customer problems and highlight appropriate solutions

  • Proven track record of self-sourcing opportunities at large organizations 

  • Ability to develop relationships with senior leaders and C-level executives

  • Experience using Salesforce (or other CRMs), sales automation tools such as LinkedIn Sales Navigator, and web conferencing tools

  • A proactive mindset with strong organizational and time-management skills

  • Self-aware individual who is eager to contribute feedback and ideas

  • Excellent presentation skills to connect with prospective clients on the phone and through delivering demos

  • Ability to thrive and adapt in a fast-paced startup culture along with highly motivated and passionate team members 

  • Possess the ability and interest to try new things and not afraid to take on a challenge independently interested in contributing to enhancing Loopio’s marketing initiatives

  • Post-Secondary Degree or equivalent 

Where You’ll Work

  • Loopio is a remote-first workplace because we recognize the advantages of working flexibly. We have Hub Regions spanning across Canada, UK, and India, which means that employees live and work remotely within a 300 KM radius of Toronto (within Ontario),Vancouver (within British Columbia), Ahmedabad (within Gujarat), Pune (within Maharashtra), and London (UK) and work within regular business hours in their timezone. 

  • Loopio has two flexible co-working locations available to Loopers in ON and BC. Those based in ON have the flexibility of working out of our convenient coworking space located in the heart of Downtown Toronto and a 12-minute walk from Union Station. BC Loopers have the option to work from our co-working office in Gastown Vancouver. It is whatever works best for you!

  • You’ll collaborate with your teams virtually (we’re just a Zoom call away!) and have established core sync hours and focus time during the workday to enable us to work smarter together

Why You’ll Love Working at Loopio

  • Your manager supports your development by providing ongoing feedback and regular 1-on-1s 

  • You have tons of autonomy and responsibility: this role provides an opportunity to try new things and push creative boundaries

  • You’ll learn more than you thought was possible; our team is obsessed with personal and professional growth (every Looper receives a professional mastery allowance each year)

  • You’ll be set up to work remotely with a MacBook laptop, a monthly phone and internet allowance, and a work-from-home budget to help get your home office all set up! 

  • Join us in regular company socials, AMA (Ask-Me-Anything), and quarterly kick-off to celebrate the big wins and milestones as #oneteam!

  • You’ll be joining a culture that has thoughtfully built out opportunities for connections in a remote first environment.

  • We have Employee Resource Groups, various fun virtual activities, and many more moments for us to have fun and learn together! 

  • You’ll be a part of an award-winning workplace and one of Canada’s fastest growing companies with ample opportunity to make a big impact here!

We recognize that all too often, potential candidates don’t apply for a position simply because they don’t hit every single criteria included in the job description—particularly members of underrepresented groups


Whether or not your experience checks off all the boxes on a job posting, we still encourage you to apply to ensure that your application receives a review from our team. We understand that a resume can only showcase so much during the applicant stage, so we've created prompts in the application for you to share more about yourself. If you've made a career transition (or a few!), you’re self taught in a new role, or you have skills/experience you’d like to highlight, we want to hear more about what you could bring to the table.


Loopio is an equal opportunity employer that is deeply committed to building equitable workplaces that are diverse and inclusive. We actively encourage candidates from all backgrounds and lifestyles to consider us as a future employer. Please contact a member of our Talent Experience team (work@loopio.com) should you require accommodations at any point during our virtual interview processes.

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What You Should Know About Senior Account Executive, New Business (Mid-Market), Loopio Inc.

Join Loopio as a Senior Account Executive in New Business, focusing on the Mid-Market segment! Here at Loopio, we're not just about work—it's about creating solutions to simplify the manual process of responding to RFPs. With our award-winning RFP response software, our Sales team plays a crucial role in connecting potential clients with innovative technologies that drive growth. As you navigate complex sales cycles and self-source opportunities within mid-sized companies, you'll be using your strategic thinking and B2B SaaS expertise to provide tailored solutions. If you're passionate about helping organizations improve their operations and can build strong relationships, then you’re the perfect fit! Your role will involve inspiring prospects through world-class demos, delivering impactful sales proposals, and collaborating closely with various teams to ensure our clients' success. Working at Loopio means autonomy and flexibility, as we are a remote-first workplace, valuing your personal growth and career development. This is more than just a sales position; it's about making a real impact together in a supportive environment where every Looper is empowered to succeed. If you're excited to help shape the future of the proposal space while achieving your professional goals, Loopio is where you belong!

Frequently Asked Questions (FAQs) for Senior Account Executive, New Business (Mid-Market) Role at Loopio Inc.
What are the responsibilities of a Senior Account Executive at Loopio?

As a Senior Account Executive at Loopio, you will play a critical role in generating new business revenue within the Mid-Market segment. Your responsibilities include driving sales opportunities, partnering with the Sales Development team to prospect target accounts, delivering compelling demos of the Loopio platform, and managing the entire sales cycle. Additionally, you'll be negotiating sales proposals and collaborating closely with customer experience teams to ensure clients' success.

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What qualifications do I need to become a Senior Account Executive at Loopio?

To become a Senior Account Executive at Loopio, you should have a minimum of 5 years of sales experience in a B2B SaaS environment. A proven track record in managing complex sales cycles and self-sourcing opportunities is essential. You should possess excellent presentation skills, strong organizational abilities, and a proactive, self-starter mindset. Experience with Salesforce or other CRMs is also required.

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How does remote work culture operate at Loopio for Senior Account Executives?

Loopio is proud of its remote-first culture, allowing Senior Account Executives the flexibility to work from home or co-working spaces based on their preferences. This means you'll collaborate with your teammates virtually and have synchronized core hours to work smarter together. Importantly, you’ll have access to a work-from-home budget and necessary hardware, ensuring you're set up for success regardless of your location.

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What does success look like for a Senior Account Executive at Loopio?

Success for a Senior Account Executive at Loopio is defined by exceeding quarterly sales targets and consistently delivering accurate forecasts. You will be expected to build strong relationships with prospective clients, support their success as customers, and contribute to the growth of Loopio's sales organization. Engaging proactively with the product team to influence platform development based on market trends is crucial.

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What initiatives does Loopio have for personal and professional growth for its Senior Account Executives?

At Loopio, we prioritize personal and professional growth through various initiatives, such as a professional mastery allowance for every Looper. You’ll receive ongoing feedback and mentoring from your manager, encouraging continuous development. You'll also have the autonomy to propose new ideas and try innovative approaches, creating a nurturing environment for your career trajectory.

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Common Interview Questions for Senior Account Executive, New Business (Mid-Market)
How do you approach prospecting for new clients as a Senior Account Executive?

In answering this question, detail your methods for identifying potential clients, such as using CRM tools or networking. Highlight how you prioritize building relationships and understanding the needs of prospects, as well as the importance of self-sourcing opportunities, enriching your pipeline for better results.

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Can you describe a successful complex sales cycle you managed?

When addressing this question, narrate a specific instance where you handled a complex sales cycle. Discuss the challenges you faced, the stakeholders involved, and how you navigated through the process to secure the deal, while emphasizing your strategic thinking and problem-solving skills.

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What techniques do you use to connect with C-level executives?

Focus on your ability to understand the unique pressures C-level executives face. Discuss fostering meaningful relationships, using tailored value propositions, and illustrating how Loopio's solutions can address their specific pain points and contribute to their overall goals.

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How do you handle objections during a sales presentation?

Share your strategies for turning objections into opportunities for deeper conversation. Discuss actively listening to the concerns of the prospect, empathizing with them, and providing data-backed responses that demonstrate how Loopio's solutions can alleviate their objections.

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Tell me about a time you exceeded your sales targets. What was your strategy?

Provide specific examples of how you set ambitious goals and the strategies you implemented to surpass them. Highlight your tenacity, creativity in problem-solving, and ability to capitalize on market opportunities, underscoring your results-focused mindset.

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How do you stay organized and manage your time as a Senior Account Executive?

Discuss the productivity tools and techniques you utilize to prioritize tasks effectively and maintain organization. Mention your approach to balancing various stages of sales cycles, including prospecting, follow-ups, and closing deals to ensure nothing falls through the cracks.

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What role does team collaboration play in your sales process?

Explain how collaborating with other teams, such as Sales Development and Customer Experience, can enhance the sales process. Provide examples of how communication and teamwork have directly influenced your sales success and the overall customer experience.

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How do you learn about market trends to enhance your sales strategy?

Describe the methods you use to keep informed about industry trends, competitor activities, and customer needs. Detail how this knowledge assists you in identifying market gaps and improving your sales pitch to resonate with potential clients.

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What do you think sets Loopio apart from its competitors?

Research about Loopio's unique selling points and articulate them based on your understanding. Identify aspects like the superior functionality of the RFP software, exceptional customer support, or innovative features, indicating your insight into Loopio's strengths.

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What motivates you to succeed in sales?

Share your intrinsic motivations for thriving in sales, whether it's supporting clients, achieving personal goals, or making a significant impact on the organization. Connect this to how working at Loopio aligns with your aspirations and drives you to excel in your role.

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Founded in 2014, Loopio offers a RFP response solution which streamlines the way enterprises respond to Requests for Proposals (RFPs), Requests for Information (RFIs), Due Diligence Questionnaires (DDQs), and Security Questionnaires. The company i...

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Full-time, remote
DATE POSTED
January 3, 2025

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