Chief of Staff, PreSales Collective

On-Target Earnings (OTE): $150k - Includes the base salary of $120-130k per year, commission-based bonuses, and equity in Sylva

Location: Remote, US-Based

About Sylva and PreSales Collective

Sylva is on a mission to build belonging by acquiring, launching, and growing professional communities. With over 1 million total members across several properties, Sylva is profitable and experiencing rapid growth. The PreSales Collective (PSC) is a global community of over 50,000 presales professionals, designed to empower its members with resources, relationships, and opportunities for personal and professional growth.

Position Overview

The PreSales Collective is seeking a hands-on Chief of Staff who will directly own and drive our enablement sales process while supporting broader strategic initiatives. This role combines direct revenue responsibility with strategic planning and operational leadership. You'll be expected to roll up your sleeves and operate at all levels of the business – from personally closing deals to shaping our go-to-market strategy and supporting executive initiatives.

Responsibilities

• Direct Sales Ownership & Execution (Primary Focus)
  • Own the full sales cycle for PSC's enablement offerings, from prospecting to close
  • Meet or exceed quarterly and annual sales quotas for enablement programs
  • Build and nurture relationships with potential and existing customers
  • Collaborate with existing customers to expand accounts and ensure renewals
  • Track sales metrics and provide regular pipeline and revenue forecasts
  • Develop and execute tactical sales strategies to drive growth
• Go-to-Market Strategy
  • Develop and implement GTM plans for PSC's enablement portfolio
  • Collaborate with marketing on demand generation initiatives
  • Identify new market opportunities and competitive positioning
• Strategic & Financial Support
  • Partner with leadership on quarterly planning and annual budgeting
  • Support financial analysis and forecasting for enablement products
  • Provide data-driven insights to inform strategic decisions
• Community & Operations
  • Support community initiatives and strategic projects as needed
  • Represent PSC at key industry events and with strategic partners
  • Help improve internal processes to increase operational efficiency

About You

• 5+ years of experience in presales, B2B sales, or customer-facing roles
• Strategic thinker who thrives in ambiguity and can navigate from high-level vision to tactical execution
• Strong business acumen with experience in sales operations, revenue operations, planning, or strategy
• Exceptional communication and relationship-building skills at all organizational levels
• Data-driven approach to decision-making and performance optimization
• Demonstrated ability to lead cross-functional projects and influence without direct authority
• Growth mindset with eagerness to take on expanding responsibilities
• Passion for the presales profession and commitment to community building

Why This Role is Unique

• Dual Impact: Directly drive revenue while helping shape PSC's strategic direction
• Career Acceleration: Gain visibility and experience across multiple business functions, positioning you for future executive leadership
• Network Development: Build relationships with the top minds in presales and establish yourself as a leader in the industry
• Learning Environment: Develop broader business competencies while working alongside experienced community builders

This role is ideal for an ambitious professional from a presales or B2B sales background who is ready to expand beyond traditional customer-facing roles into business strategy and operations. If you're excited to roll up your sleeves, navigate ambiguity, and help usher PSC into its next evolution as the #1 presales community, we want to hear from you.