Sales Development Representative (Pittsburgh)

Who we are:

At Opkey, we empower enterprises to unlock the full potential of their ERP investments with cutting-edge, agentic AI-powered automation. Our intelligent platform delivers continuous assurance across the entire ERP lifecycle; from initial deployment to day-to-day operations and long-term digital transformation.

By eliminating manual errors, accelerating testing cycles, and ensuring seamless adoption of critical updates, Opkey helps organizations modernize with confidence and agility. Trusted by 250+ global enterprises, we reduce risk, drive efficiency, cut costs, and fast-track innovation; so businesses can focus on what they do best: growing and evolving in a dynamic digital world.

We’re Looking for a Hustler. A Connector. A Spark That Starts the Fire.

Opkey is looking for a Sales Development Representative (SDR) who’s ready to kick off big conversations—and even bigger opportunities. This role isn’t about waiting for leads to land in your lap. It’s about creating momentum, starting smart conversations, and laying the foundation for enterprise deals.

You’re a natural communicator—curious, confident, and persistent. You love researching accounts, finding the right people, and crafting messages that break through the noise. You’re the type who thrives in a fast-paced environment and loves the energy of a team chasing big goals. This is a high-visibility, high-growth role that will set you up with enterprise SaaS sales experience from day one.

This role is in-office 5 days a week in our beautiful, modern coworking space in Downtown Pittsburgh , alongside a collaborative and ambitious team.

What You’ll Own

• Prospect with Purpose
• Identify and research target accounts, key decision-makers, and the right timing for outreach. Use cold calls, emails, LinkedIn, and creative tactics to start conversations that matter.
• Qualify Leads Like a Pro
• Understand prospect needs, pain points, and buying readiness using qualification frameworks like BANT. Pass only the best opportunities to Account Executives.
• Drive Pipeline
• Own the top of the funnel and help keep it full. You’ll play a critical role in building a steady stream of qualified leads that fuel the sales team’s success.
• Collaborate & Connect
• Work closely with Account Executives to develop account strategies, share insights from your outreach, and support smooth handoffs of qualified opportunities.
• Educate & Influence
• Share Opkey’s value proposition, explain our automation platform’s benefits, and handle initial objections with clarity and confidence.
• Track & Optimize
• Keep your CRM (HubSpot) clean and updated. Monitor your metrics and continuously improve your outreach based on what’s working.
• Be the Feedback Loop
• Capture trends and objections from the market. Share what you’re hearing with marketing and product teams to help shape our go-to-market message.

As a Sales Development Representative at Opkey, you will be responsible for generating qualified pipeline through strategic outbound prospecting and account engagement. Working alongside Account Executives, Marketing, and Sales Leadership, you will identify opportunities within enterprise organizations and initiate conversations with key decision-makers across Oracle, Workday, Salesforce, and other enterprise application environments.

In this role, you will:

• Research target accounts, identify buying centers, and build prospecting strategies aligned to account priorities.
• Execute high-volume, personalized outreach through phone, email, LinkedIn, and other outbound channels to generate qualified meetings.
• Partner with Account Executives to develop account plans, coordinate outreach efforts, and support strategic opportunity creation.
• Leverage market trends, product updates, and industry insights to deliver relevant and timely messaging to prospective customers.
• Qualify prospective customers by understanding business challenges, current processes, and organizational priorities before transitioning opportunities to the Account Executive team.
• Maintain accurate activity, account, and opportunity data within HubSpot to ensure pipeline visibility and reporting accuracy.
• Collaborate cross-functionally with Marketing, Product, and Customer teams by sharing customer feedback, market trends, and competitive insights.
• Participate in ongoing coaching, sales enablement, team meetings, and professional development initiatives designed to strengthen your sales skills and accelerate career growth.

This role offers the opportunity to develop expertise in enterprise SaaS sales while working with some of the world's largest organizations. Success in this position is measured by your ability to consistently generate qualified pipeline, build strong relationships with prospective customers, and contribute to the overall growth of the sales organization.

What You’ll Bring

• 0–2 years of sales or business development experience (internships or campus ambassador roles count!)
• Excellent verbal and written communication—you can explain, persuade, and connect with clarity
• A self-starter mindset—you’re proactive, organized, and thrive when you’re driving your own success
• Confidence to pick up the phone, ask smart questions, and handle objections with poise
• CRM familiarity (we use HubSpot) and comfort working in tools like LinkedIn Sales Navigator, ZoomInfo, or similar
• An interest in SaaS, enterprise tech, or automation—bonus points if you’ve sold into IT or operations teams
• A desire to grow into a full-cycle sales or account executive role long term

Where This Role Can Take You

This is more than a sales job—it’s a career-building opportunity. Top-performing SDRs will have a clear path to promotion into the Account Executive role , with mentorship, skill-building, and real-time coaching along the way. You’ll gain experience in enterprise SaaS sales, outbound strategy, and cross-functional collaboration—giving you the toolkit to grow into a quota-carrying AE role within 12–18 months.