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Sierra Interactive Senior Sales Manager



Sales & Business Development
Posted on Wednesday, June 5, 2024

About the company:

Sierra Interactive develops a full-suite residential real estate tech platform for teams and brokers in the U.S. and Canada. Sierra’s proven lead generation and management solutions are trusted by top-performing teams and influential coaches in the real estate industry. Founded in 2007, Sierra has a remote-first workforce across the U.S. We are a high-growth, private-equity backed company with big bold goals, and that’s where you come in.

About this role:

We are seeking a Sr. Sales Manager to lead a high-performing sales organization that achieves ambitious YOY growth goals. The Sr. Sales Manager must execute a repeatable, scalable revenue process driven from data, technology and enablement, and be an effective leader of front-line sales talent. Initially in a player/coach role, the ideal candidate is scrappy, resourceful, resilient and a culture-carrier as they help evolve the sales organization. We’re looking for a “seller’s manager” with a proven track record of leading sellers to hit or exceed quotas in a high-velocity SMB sales motion. You must have experience building, engaging, retaining and managing teams through change, particularly in a remote setting, and you also have demonstrated that you can develop, drive and measure programs that contribute to pipeline, including outbound and inbound motions. You’re a good fit if you have worked in a real estate SaaS company before and have proven experience growing companies in the $15-45m revenue range. This role reports directly to the Vice President of Growth.

Day-to-Day, you will:

  • Develop a comprehensive understanding of the Sierra product offering, real estate industry, competitive landscape and market trends to effectively position the company in the market.
  • Deeply understand the sales process and train the sales team on what to do; provide regular call and deal management coaching.
  • Conduct regular 1:1 and group pipeline review and forecast meetings; qualify deal advancement issues and coach reps on how to control opportunities.
  • Enforce clear pipeline management rules, including entry/exit criteria for each lifecycle stage.
  • Develop sales enablement resources to drive consistency and increase seller effectiveness.
  • Carry a personal quota to demonstrate what good looks like, build an industry network and deeply understand customer needs and industry and macroeconomic trends.
  • Join critical prospect-facing meetings to support AEs.
  • Determine appropriate org to support growth goals; assess reps’ strengths and weaknesses; hire & train A-players and replace underperformers.
  • Build a winning culture by setting appropriate team and individual goals and holding all accountable toward progress against those goals.
  • Act upon areas of growth identified in semi-annual engagement surveys and through other feedback mechanisms.
  • Mentor, inspire, and develop our existing sales team. Invest time in and provide ongoing training and development opportunities to help sellers develop their sales skills and grow their careers.
  • Act as a culture-carrier and effectively manage through change, maintaining a relentlessly positive attitude inspiring others to do the same.
  • Ensure cross-functional alignment to achieve pipeline objectives.
  • Manage executive and team level dashboards to showcase performance KPIs across products and sales funnels.
  • Experiment with initiatives to open new lead generation channels and sales tactics/strategies
  • Be an active presence at industry events and build/own an industry network by connecting personally with key clients, prospects and partners.
  • Continuously develop personal leadership, hiring and training skills.


  • 2+ years managing a sales team of 2 or more sellers.
  • Real estate SaaS experience is highly preferred. SaaS selling experience required.
  • Experience with HubSpot and Gong preferred.
  • Demonstrated experience growing companies in the $15-$45M revenue range and selling/managing in a high velocity SMB sales motion with deals ~$500-1,000 MRR.
  • Track record of achieving team quota with 75% of sellers achieving individual targets.
  • Experience reporting to a member of the leadership team (VP or higher).
  • Experience building, engaging, retaining and managing teams through change - particularly in a remote setting.
  • Proven experience measuring and driving the programs that contribute to pipeline, including outbound and inbound motions.
  • Ability to master the customer conversation with specific personas and use cases; demonstrated demo, negotiation and closing skills.
  • Active listener and excellent communicator who can establish credibility and trust quickly and who has the ability to persuade others.
  • Demonstrated experience working with a revenue operations team to establish a consistent, reliable source of sales data and analytics and data tracking rhythms to improve OKRs month over month.
  • Execution-oriented with a high GSD quotient.
  • Competitive, coachable and curious - a self-starter.
  • Trained on sales frameworks like MEDDICC, Sandler, Challenger, BANT and can apply them to drive outcomes.
  • Strategic thinker with an ability to build / augment GTM strategy and identify opportunities for improvement.
  • Operationally oriented and can translate market-level perspectives into an operational plan.
  • Highly motivated with an intrinsic desire to move things forward fast; demonstrates a willingness to go above and beyond to get a deal done.
  • Demonstrates humility with a willingness to hit the phones and execute discovery, demos and close deals
  • Ability to travel occasionally.
  • U.S. Resident

Compensation and Benefits:

  • OTE of ~$180,000 annually
  • 100% remote work.
  • Paid holidays and paid time off and personal days
  • Company-provided health / vision / dental insurance for the employee
  • 401k retirement employer matching contributions (up to 4% matching)