Hard work pays off on the daily.
Account Executive, Small-to-Medium Enterprise
Location
United States
Posted
2 days ago
Salary
$100K / year
Seniority
Senior
Job Description
Account Executive, Small-to-Medium Enterprise
DailyPay
• Full-Cycle Sales Management: Independently manage and execute sales cycles for companies within the SME segment (500–2,000 employees) to meet or exceed monthly quotas. • Strategic Presentation: Conduct high-impact product demonstrations via webinars and in-person meetings, effectively articulating the DailyPay value proposition to prospect champions. • Pipeline Development: Proactively build and maintain a robust pipeline of qualified opportunities using modern sales tools (Salesforce, Salesloft) and outbound prospecting techniques. • Stakeholder Navigation: Identify and engage with key influencers and decision-makers across HR, Finance, and Operations departments to build consensus. • Data-Driven Consulting: Utilize DailyPay’s analytical tools to present clear business cases, highlighting employee benefit ROI and retention improvements for partners. • Contract Negotiation: Manage and facilitate the negotiation of service terms and agreements with prospect decision-makers, ensuring alignment with company guidelines. • Cross-Functional Collaboration: Partner with Sales Development and Implementation teams to ensure a seamless transition of accounts and long-term partner success. • Market Intelligence: Maintain up-to-date knowledge of the HCM and Fintech landscape to effectively handle objections and position DailyPay against competitors
Job Requirements
- Proven Sales Track Record: 3+ years of experience in B2B sales (SaaS, HR technology, or financial services preferred), with a history of meeting or exceeding quotas.
- Consultative Skills: Demonstrated ability to build trust with stakeholders and navigate mid-market corporate structures.
- Communication Excellence: Strong verbal and written communication skills, with professional fluency in presenting technical product features to non-technical audiences.
- Analytical Mindset: High level of business acumen with the ability to interpret data and use financial tools to communicate value.
- Operational Discipline: Exceptional detail orientation and organizational skills, specifically regarding CRM hygiene and pipeline management.
- Adaptability: A coachable, resilient mindset with the ability to thrive in a fast-paced environment and adapt to evolving sales strategies
Benefits
- Exceptional health, vision, and dental care
- Opportunity for equity ownership
- Life and AD&D, short- and long-term disability
- Employee Assistance Program
- Employee Resource Groups
- Fun company outings and events
- Unlimited PTO
- 401K with company match
Related Guides
Related Job Pages
More Account Executive Jobs
Account Executive
CohereAt Cohere, our mission is to build machines that understand the world, and to make them safely accessible to all.
• Focus on net-new logo acquisition via outbound business development activity and relationship building with key stakeholders. • Work closely with customers and prospects as a trusted advisor who deeply understands their challenges and goals, and will tailor solutions to drive impact for their businesses. • Work in close partnership with channel partners to find opportunities to scale outreach and customer satisfaction in your region. • Collaborate with Product and Engineering teams on strategic motions to deliver solutions to large enterprise customers. • Collaborate with Sales Development Representatives to drive top of funnel activity. • Own the full sales cycle – from initial outreach through proof-of-concept to deal close.
Account Executive
CohereAt Cohere, our mission is to build machines that understand the world, and to make them safely accessible to all.
• Focus on net-new logo acquisition via outbound business development activity and relationship building with key stakeholders • Work closely with customers and prospects as a trusted advisor who deeply understands their challenges and goals, and will tailor solutions to drive impact for their businesses • Work in close partnership with channel partners to find opportunities to scale outreach and customer satisfaction in your region • Collaborate with Product and Engineering teams on strategic motions to deliver solutions to large enterprise customers • Collaborate with Sales Development Representatives to drive top of funnel activity • Own the full sales cycle – from initial outreach through proof-of-concept to deal close
Senior Account Executive
Inspira EducationInspira Education Group is one of the fastest-growing edtech startups in the US. We started with a simple mission to democratize access to high-quality coaching so that every student in the world has an equal opportunity to access the best opportunities. As the world’s leading network of top admissions coaches in medical, legal, business, and college studies, we’re building software and services in one place—disrupting long-entrenched application processes with products and experiences that strive to provide an equal platform for candidates from diverse backgrounds worldwide. As one of the fastest-growing edtech firms in the world, we are backed by some of the leading venture capital firms and investors in the world, including Zeev Ventures, Quiet Capital, Craft Ventures, Jeff Fluhr (Founder of Stubhub), and David Sacks (Former COO of PayPal and Founder of Yammer).
Role Description We’re currently hiring Senior Account Executives across multiple Inspira Education Group brands. We’re looking for a driven, entrepreneurial Senior Account Executive with a strong ownership mindset. Someone who thrives in a fast-paced, mission-driven environment and is eager to help students achieve their academic dreams. You’ll play a key role in driving revenue growth through inbound sales, while also helping to build and refine the systems and processes that will allow our sales function to scale in the future. This is one of the most impactful roles at Inspira. As the first point of contact for parents and students exploring our programs, you’ll set the tone for their entire experience. The trust, empathy, and expertise you bring to these conversations often become the deciding factors in their choice to work with us. You’ll guide them through one of the most meaningful decisions of their lives - investing in their education and future success. What You'll Do - Lead consultative intro calls (inbound) with parents and students to understand their goals, explain the admissions process, and recommend the right Inspira programs and packages based on their needs. - Own the relationship with prospective students and families from first touch through enrollment by building trust, offering guidance, and ensuring a smooth and positive experience throughout their journey. - Follow up strategically and consistently to stay connected with prospects, anticipate questions or concerns, and help them confidently decide to partner with Inspira. - Experiment and innovate—test new scripts, refine messaging, and explore creative follow-up strategies to maximize conversion rates and continuously improve the enrollment experience. - Close deals across a range of programs and services, meeting or exceeding monthly and quarterly sales goals. - Collaborate cross-functionally with the marketing, counseling, and finance teams to ensure seamless handoffs, strong alignment, and an exceptional customer experience. - Stay informed on competitor offerings and market trends; provide real-time feedback to founders and leadership to shape product, pricing, and go-to-market strategy. - Leverage HubSpot CRM to manage the full sales cycle—tracking leads, logging communications, creating email templates, forecasting revenue, and maintaining data integrity across all stages. - Forecast enrollments accurately by managing deal stages, values, and close dates in HubSpot. - Support onboarding and customer success for newly enrolled students to ensure a strong start and high satisfaction. Qualifications - 3–5 years of experience in inbound sales within a service-oriented or consultative environment, ideally with sales cycles under 2–3 months. - Proven success selling premium or high-value service packages (ACV $5,000+), with a track record of exceeding targets and delivering exceptional client experiences. - Excellent communication skills. You’re confident presenting, writing, and speaking with clarity, empathy, and professionalism. - Strong CRM proficiency, preferably in HubSpot (or similar tools), with a knack for maintaining clean data and using systems to drive performance. - Comfort with data and reporting, including experience using Excel or Google Sheets to build and interpret dashboards. - Nice to Have: Prior experience in education, admissions, or academic consulting sales. What We Value - Winning Attitude: You find a way to succeed. You dig deeper to understand the “why” behind a no, and you don’t stop until you’ve found a solution. - Curiosity: You constantly push yourself to learn, experiment, and improve. You’re open to new ideas and you see setbacks as opportunities to grow. - Genuine Relationships: You lead with empathy and integrity. Parents and students trust us with one of the most important decisions of their lives, and you honor that by building authentic, human connections. - Smart and Hard Work: You combine awareness and judgment with effort and discipline. You know when to think strategically and when to roll up your sleeves. - Humility and Teamwork: You celebrate collective success over individual wins. You welcome feedback, learn from mistakes, and support those around you. Benefits - Amazing people with a great vision and values. - Mission-driven team culture focused on student success. - Your work directly impacts the lives and careers of students across the globe. - Health, dental, and vision insurance, base plans 100% employer paid. - Flexible paid time off (PTO) and paid holidays. - 401(k) with company match. Compensation OTE: $200K+
Enterprise Acquisition Account Executive
DynatraceDynatrace is a global application performance management software firm and a former member of Compuware. As an employer, the company is in support of helping it
Your role at DynatraceAs an Enterprise Acquisition Account Executive, you will play a pivotal role in expanding Dynatrace's presence across Alberta's largest and most influential organizations. Based in Calgary, you will focus on helping enterprise customers accelerate digital transformation, modernize critical applications, improve operational resilience, strengthen security posture, and prepare for the next wave of AI-driven innovation. This is a true hunter role, focused on creating new opportunities and developing strategic relationships across a carefully curated territory of approximately 40 enterprise accounts. You'll engage senior business and technology leaders within Alberta's key industries, including Energy, Oil & Gas, Utilities, Financial Services, Telecommunications, Transportation, and Industrial organizations, helping them understand how Dynatrace can deliver measurable business value and transform the way they operate. Success in this role requires more than closing deals. It means becoming a trusted advisor who can connect technology investments to tangible business outcomes such as increased operational efficiency, improved reliability, reduced risk, enhanced customer experiences, and accelerated innovation. Working alongside a world-class team of Sales Engineers, SDRs, Customer Success Managers, Alliance Partners, and Sales Leadership, you will be empowered to drive meaningful impact for your customers while building a high-growth territory for Dynatrace. What You Will Be Focusing On as an Enterprise Acquisition Account Executive - Execute a strategic territory plan across Alberta's largest enterprise organizations to maximize revenue growth and market expansion. - Drive net-new logo acquisition through a disciplined land-and-expand approach, identifying opportunities to establish Dynatrace as a strategic platform within enterprise accounts. - Build and nurture executive relationships with CIOs, CTOs, CISOs, VP Operations, VP Technology, Digital Transformation leaders, and other senior decision-makers. - Lead business-value conversations that align Dynatrace solutions with customer priorities such as operational excellence, system reliability, cybersecurity, AI adoption, cloud transformation, and customer experience. - Develop compelling business cases that demonstrate measurable financial and operational impact for customers. - Engage organizations navigating complex modernization initiatives, including cloud migration, digital transformation, infrastructure modernization, application modernization, and AI-driven innovation. - Generate pipeline through targeted prospecting, executive engagement, industry events, strategic partner collaboration, and account-based initiatives. - Leverage Alberta's strong ecosystem of technology partners, cloud providers, systems integrators, and consulting organizations to accelerate opportunity creation and customer success. - Navigate complex enterprise sales cycles involving multiple stakeholders, technical evaluations, procurement teams, and executive sponsors. - Collaborate closely with Sales Engineering, Customer Success, Marketing, Alliances, and Leadership teams to build winning account strategies. - Create multi-threaded relationships across business and technology teams to drive broad adoption and long-term customer partnerships. - Ensure customers achieve measurable business outcomes, helping them realize the full value of their investment while establishing Dynatrace as a trusted strategic advisor. What will help you succeedSuccess in this role comes from your ability to uncover strategic business initiatives, align technology solutions to measurable outcomes, and build trusted executive relationships within complex enterprise organizations. You are naturally curious and business-oriented, capable of understanding the operational challenges faced by Alberta's largest organizations and translating those challenges into transformational opportunities. You understand that enterprise buyers are focused on outcomes—not just technology—and you know how to connect observability, security, cloud modernization, and AI initiatives to operational performance, business resilience, efficiency gains, and revenue growth. You thrive in high-performance environments and are energized by building new markets, opening doors within strategic accounts, and helping customers solve meaningful business challenges. You combine strong prospecting discipline with executive presence, allowing you to confidently engage C-level leaders and influence strategic decision-making. You know how to navigate complex enterprise environments, build consensus across multiple stakeholders, and maintain momentum through long sales cycles. Most importantly, you are motivated by creating value—both for your customers and your business—and are driven by delivering measurable impact in every customer engagement. Preferred Requirements - 5+ years of successful Enterprise Software or SaaS sales experience with a demonstrated track record of acquiring new enterprise customers. - Proven ability to consistently exceed quota through new logo acquisition and strategic territory development. - Experience selling into large enterprise organizations within Alberta or Western Canada. - Experience engaging organizations within Energy, Oil & Gas, Utilities, Financial Services, Telecommunications, Transportation, Industrial, Manufacturing, or Midstream sectors. - Demonstrated success building relationships with CIOs, CTOs, CISOs, VP Technology, VP Operations, and other executive stakeholders. - Proven ability to lead value-based sales motions focused on measurable business outcomes, operational improvements, risk reduction, and return on investment. - Experience developing business cases and executive-level value propositions that align technology investments to strategic business priorities. - Strong prospecting and pipeline generation capabilities with a proven ability to create opportunities within targeted enterprise accounts. - Experience managing complex enterprise sales cycles involving multiple decision-makers, technical evaluations, executive sponsorship, procurement processes, and commercial negotiations. - Experience collaborating with cloud providers, systems integrators, consulting firms, and channel partners to accelerate growth and customer success. - Strong territory planning, account planning, forecasting, and sales execution skills. - Exceptional communication, presentation, negotiation, and executive engagement abilities. - Familiarity with disciplined enterprise sales methodologies such as MEDDPICC. - Experience selling observability, cybersecurity, cloud, infrastructure, DevOps, AIOps, platform engineering, or enterprise technology solutions. - Strong understanding of the unique business, operational, and technology challenges facing Alberta's enterprise market. - Entrepreneurial mindset, high degree of accountability, and a passion for helping customers create lasting business value through technology. Why you will love being a Dynatracer - Dynatrace is a leader in unified observability and security. - We provide a culture of excellence with competitive compensation packages designed to recognize and reward performance. - Our employees work with the largest cloud providers, including AWS, Microsoft, and Google Cloud, and other leading partners worldwide to create strategic alliances. - You'll get to work at the forefront of innovation with Dynatrace Intelligence—the industry's first agentic operations system. Bringing together deterministic and agentic AI, it helps teams understand what's happening, why it matters, and what to do next— automatically. - Over 50% of the Fortune 100 companies are current customers of Dynatrace.


