Senior Account Executive

TrueDialog, Inc.
Chicago, IL

We are prioritizing candidates currently based in Austin, TX for a hybrid (3x/week in-office and 2x/wk from home office) but are open to candidates based anywhere else in the U.S. (for a Remote home office arrangement).

Join a rapidly growing company that has demonstrated impressive year-over-year growth, consistently exceeding key performance metrics and driving industry-leading results. With a focus on innovation and sustainable growth, we're expanding quickly and looking for driven individuals to join our mission to make it easy for organizations to connect, engage, and succeed in the modern world.

Company Overview

Based in Austin, Texas, TrueDialog is a Communications Platform-as-a-Service (CPaaS) company that offers an enterprise-grade SMS messaging platform designed for businesses of all sizes. Our award-winning platform is transforming how organizations connect with customers through text messaging - today's most engaging and responsive channel - with powerful capabilities and simplified implementation.

Through superior features, industry-leading security, and direct carrier connections, the platform deliver enterprise-grade reliability while reducing messaging costs by up to 75%. TrueDialog is trusted by thousands of brands, including Coca-Cola, Hilton, Kansas City Chiefs, Northern Tool, SubjectWell, and Tulane University.

Position Overview

As we continue to scale our business, we are currently looking for top-tier sales talent to join our growing sales team. Reporting to the Sales Leader, Account Executives are a critical part of the company and are primarily responsible for the growth of ARR within new customer acquisition and customer expansion. Candidates must have strong experience full-cycle selling of SaaS software to sales and marketing personas. 

As brand representatives, ideal candidates have strong business acumen, a professional video presence, and excellent active listening skills. They will be required to be able to explore and understand customers’ businesses, their operational challenges and eloquently articulate the value of the TrueDialog solution. We’re looking for intrinsically-motivated closers with a high level of integrity and self-discipline to work in a fast pace, ever-changing environment, delivering impactful results to the business.

Responsibilities

  • Building Pipeline and Making Quota: Achieve or exceed revenue targets each quarter towards an annual $500-600K quota, as well as build a solid pipeline that can realistically meet and exceed both short and long term goals
  • Full Sales Cycle Management: Own and manage the entire net new sales cycle from prospecting and lead generation to security evaluation, to contracting, to closing deals, ensuring consistent engagement, persistent forward motions, and follow-through.
  • Outbound Prospecting: Actively generate new business opportunities through cold calling, emailing, networking, and social selling in targeted verticals, working with ABM signals and independently sourcing up to 50% of your own pipeline
  • Inbound Lead Qualification: Respond promptly to inbound leads, qualify prospects in or out, and conduct discovery calls to understand customer needs and pain points.
  • Solution Selling: Present and demonstrate the company’s products/services, tailoring solutions to meet the specific requirements of prospects in targeted verticals, leveraging MEDDIC, MEDPIC, SPICED, Sandler or other sales methodology
  • Relationship Building and Management: Establish and nurture long-term relationships with key decision-makers, maintaining a strong network within assigned verticals to ensure repeat business and referrals.
  • Pipeline Management and Forecasting: Maintain an accurate and up-to-date sales pipeline in Salesforce CRM, providing forecasts and ensuring timely follow-up to close deals within target timeframes.
  • Collaboration with Cross-functional Teams: Collaborate with marketing, finance, product, and customer success teams to align strategies, create targeted campaigns, and ensure customer satisfaction post-sale.
  • Effective Presentation Skills: Deliver compelling, tailored presentations and conduct tailored demonstrations to prospective clients, clearly articulating product value and aligning solutions to their specific business needs in a way that drives engagement and fosters trust.

The following qualities are essential:

  • Strong Communication Skills: The ability to convey complex ideas clearly and persuasively, both in writing and verbally, is critical for engaging clients and stakeholders. You will be responsible for enthusiastically conveying TrueDialog’s story.
  • Resilience and Professional Persistence: A resilient mindset and persistent action are essential for overcoming obstacles and rejections, and to see average sales cycles of 2-8 months through to close.
  • Solution-Oriented Mindset: The ability to listen to client needs and offer tailored solutions that address their specific business challenges and objectives
  • Strategic Thinking: The ideal candidate has a natural curiosity and will be able to assess market trends, understand the competitive landscape, and present thoughtful business cases throughout the sales cycle, along with an ability to anticipate outcomes and potential breakpoints that can derail a deal.
  • Discipline, Time Management, and Organization: Managing multiple leads, opportunities, and tasks efficiently is crucial to staying on top of your book of business. Organizing each day and the daily activities to produce 60+ activities per day is required
  • Customer-Centric Attitude: Focusing on the client’s success, rather than just the sale, ensures stronger relationships and increased customer loyalty, paving the way for upsell and cross-sell opportunities.
  • Metrics-Driven & Goal Oriented: With the ability to understand and follow key performance indicators (KPIs), consistently striving to exceed targets.
  • High Integrity and Positive Attitude: Maintaining optimism and enthusiasm even in the face of obstacles, and inspiring others around you to stay motivated and focused is key.

Requirements

  • 5+ years of experience in a B2B software sales position selling CPaaS, SMS, communication tools or MarTech with an annual quota of $500K-600K or more.
  • Proven track record of meeting or exceeding quota, selling mid-market and enterprise deals with an ACV ranging between $25K-$50K ARR to Marketing, Sales and Customer Success teams
  • Experience selling to HigherEd, Sports & Entertainment, SaaS, Financial Services, Healthcare, Construction, Marketing Agencies, or other specific verticals
  • Proven experience selling to buying teams by identifying and working all stakeholders across the business
  • Proficiency in and successful use of a proven sales methodology such as MEDDIC, MEDDPICC, SPICED, Sandler, Challenger, Solution Selling, Value Selling, etc.
  • Strong operating experience with CRMs (Salesforce), workflow/sequencing tools (Outreach, Salesloft, Apollo, etc.), revenue intelligence tools (Gong, Clari, Ebsta, etc), social selling tools (LinkedIn Premium, Sales Navigator) and CPQ tools (PandaDoc, Docusign), and Microsoft Teams
  • Must have high integrity and be an honest, truthful, authentic human.
  • Bachelor’s Degree or equivalent

Benefits

  • Dynamic Work Environment: Join a passionate team in a fast-growing company with a strong product foundation, proven financials, and ambitious growth plans.
  • Competitive Compensation: Attractive salary and benefits package in a remote company, including 70% of employee health benefits paid, 401k, strong PTO, and professional development opportunities.
  • Growth Opportunities: Be a key player in a market that is poised for exponential growth, and scale-up environment where your insights and leadership will directly impact the company’s future
  • Innovative Culture: Work in a collaborative, forward-thinking setting that values innovation, creativity, and data-driven decision-making with a strong team and proven Executive team.
Posted 2026-01-20

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