Sales Director

Remote - Ridgefield, NJ

OSG is a global provider of leading customer engagement and payment solutions. We help clients integrate critical customer interactions to optimize working capital and drive profitable business growth. Our solutions aim to connect the entire customer experience by aligning transactional, payment, and marketing touchpoints for simplified operations and smarter engagement. Plugging into the power of our innovative technology and data-driven insights, we curate tailored, digital-first strategies for a range of industries. The goal: to modernize processes and create frictionless experiences. Our clients benefit from a partnership that values simplicity, security, and connectivity—for today's environment and tomorrow's innovation. OSG will offer you the opportunity to succeed with a solid company that provides world-class services to the top companies in the U.S. We are looking for people who want to learn and grow – and we provide on-the-job training to set you up for success!

We are seeking to add a talented Sales Director (Remote position) to our team to help support and facilitate our growth and expansion of services.

As a Senior and Experienced Sales Individual Contributor, you will have built up a wealth of sales experience selling into North America's largest and most successful companies. You are curious by nature, a superb communicator, and naturally excel in leading strategic teams to drive net-new business and high value up/cross-sell.  You thrive in a fast-paced, cutting-edge, technology-driven environment. Even though we are a highly respected and established company we operate with the passion and culture you'd expect from an exciting start-up. This isn’t just any SaaS sales role and it won’t be for everyone. Expectations are high, and the addressable market and your personal opportunity, is even greater. In fact, this role may well be the most interesting and rewarding career move you have ever made. You will be supported, coached and you’ll have the opportunity to sell a transformational solution that genuinely meets the needs of our customers and their clients. Working with our highest value customers and prospects, you will benefit from a proven track record of nurturing and cultivating stakeholder relationships at the Finance, CX, and Marketing Executive levels. You will have the opportunity to overachieve and earn uncapped commissions with accelerators based on performance.

As a key member of our sales team, you must thrive in an environment that is highly collaborative and ever evolving, leveraging both your own, and your internal resources, to win. You enjoy working in a diverse, equitable and inclusive team where people feel a deep sense of belonging and you hold yourself and others to the highest levels of performance. We need winners that will help our company grow, exceed goals and expectations, and have a whole lot of fun along the way.

 ** This position is a Remote Opportunity/ Work From Home

Key Responsibilities:

  • Drive new logo and upsell activity against accounts and prospects in assigned territory
  • Build, manage and maintain balanced pipeline for both new logo and existing clients
  • Maniacal focus on helping our clients deliver a best in class, CEM experience to the individuals they serve
  • Strategically orchestrate resources both internally and externally throughout the sales process
  • Design, demo and deliver proposals to drive key business outcomes for your clients/prospects (e.g. ROI, reduce DSOs, enhance client experience)
  • Articulate relevant value messaging across various buying roles (user, technical, payments, real estate, financial, CXO, influencer)
  • Accurately forecast profitable and predictable territory performance
  • Understand and document corporate budget decision-making timeframe, customer goals and key decision makers within the prospect’s organization
  • Qualify and close leads sourced by Marketing and/or other Demand Generation channels
  • Capture and report client or prospect account, opportunity, pipeline and other data points in
  • Partner with Client Success to successfully on-board and care for our customers

Success Criteria:

Specific KPI’s include, but are not limited to:

Booking $’s Performance vs. Quota

Product Mix Monthly Recurring Revenue

Pipeline Size & Velocity Win Rate

New Logo vs. Upsell Digital Growth

Basic Qualifications:

  • Experience selling SaaS-based MRR/ARR offerings
  • Experience with digital payments and integration (Preferred)
  • Experience with digital payments in Homeowner Association and Property Management (Preferred) 
  • Prior history selling into the C-suite, specifically CFO, CXO, CMO
  • Experience with sales tools (, Salesloft, Sales Navigator, Saleshood/Highspot)
  • Digital Transformation sales experience
  • Outstanding demonstration and presentation skill
  • Consultative selling in an in-person or virtual environment
  • Competitor: High drive, commitment to win, willingness to compete and “be the best”

Location: Remote Opportunity/Work From Home


  • PTO
  • Medical, dental, vision plans, employee assistance program, as well as life insurance and LTD plans
  • Supplemental life insurance
  • Voluntary accident and critical illness insurance, respectively
  • Flexible Spending Account available
  • 401k plan

OSG offers equal employment opportunity and will not discriminate on the bases of race, religion, color, sex (including pregnancy, gender identity, and sexual orientation), parental status, national origin, age, disability, family medical history or genetic information, political affiliation, military service, or other non-merit-based factors.


JOB CODE: 1000732