Outbound Sales Specialist

Location: Fully remote (U.S.). Standard hours are 9:00 AM–5:30 PM ET, with flexibility for West Coast schedules. Role Type: Contract, 6 months with possibility of extension About Our ClientOur client is a well-established financial technology company that helps small businesses across the U.S. manage their finances. Its platform covers cloud accounting, payroll, payments, bill pay, and live bookkeeping services. Its main customers are small business owners who are moving away from spreadsheets and desktop software toward modern, connected tools. The company is known for a culture built on integrity, courage, customer obsession, teamwork, and giving back.

Job Description: This is an outbound sales role on a high-energy, metrics-driven team. Your day will center on calling small business prospects, running consultative discovery conversations, and recommending the right solutions. You'll also manage your own pipeline and keep your CRM current. AI tools are part of the daily workflow, and you'll work with weekly contests, scored call reviews, and 1:1 coaching. The team is moving away from selling individual products and toward full-platform conversations. That means understanding a customer's entire business and tech stack, uncovering their real pain points, and recommending the right combination of solutions. The focus is on diagnosing first, not on listing features. You'll collaborate closely with front-line leaders and teammates and report to the sales manager. The ideal candidate is a curious, resilient hunter who enjoys researching accounts, building a hypothesis, asking sharp questions, and helping business owners solve real problems.

Duties and Responsibilities: Proactively call small business prospects from targeted lists and campaigns. Build and manage your own pipeline through consistent outbound prospecting. Respond to prospect signals on the same day. Research each account and industry before the call and form a hypothesis. Run consultative discovery on operations, current processes, tech stack, pain points, and goals. Recommend the right mix of accounting, payroll, payments, bill pay, and bookkeeping solutions. Guide customers through migration from desktop software to a cloud-based platform. Identify opportunities to attach additional products based on customer needs. Keep Salesforce accurate, with sales stage, next step, close date, and notes on every opportunity. Use AI tools such as Claude and Gemini for call prep, account research, and follow-ups. Meet or exceed targets for call volume, appointments, conversion, product attach, and revenue. Take part in weekly scored call reviews, 1:1 coaching, and team contests, and apply feedback quickly. Required Experience/SkillsProven experience in outbound prospecting, cold calling, and high-velocity sales. A track record of creating your own opportunities and exceeding quota. A consultative, solution-selling approach with strong discovery skills. Comfort holding business conversations with small business owners and handling objections, including difficult ones. CRM discipline, with experience in Salesforce or an equivalent system. Resilience in a high-volume environment with visible performance scoreboards. Coachability and high learning agility, since tools and processes change frequently. Ability to sell a broader platform rather than a single product.

Nice-to-Haves: Experience selling SaaS, fintech, financial, or accounting products to small businesses. Familiarity with small business accounting workflows (AP/AR, payroll, bookkeeping).Experience owning or working in a small business. Hands-on use of AI tools (Claude, Gemini, NotebookLM, or similar) in a sales workflow. Experience with power dialers, scheduling tools, Outreach, or ZoomInfo.

Pay & Benefits: Summary

Pay rate: $25.57 per hour

Incentives: Weekly and monthly performance incentives