Jake Obremski

Owned full-cycle sales for a technical SaaS platform, from outbound prospecting through close, renewal, and expansion. Built pipeline from zero and scaled the business to ~$500K ARR.

• Generated and closed net-new business through high-volume outbound (LinkedIn, email, calls), consistently managing my own pipeline
• Sold into mid-market accounts, navigating multi-threaded deals across multiple stakeholders
• Ran full sales cycle: discovery, demo, technical validation, negotiation, pilot execution, and close
• Closed deals ranging from ~$10K to $75K+ ARR, maintaining ~18% win rates on qualified opportunities
• Owned renewals and contract negotiations, proactively managing risk and driving retention
• Drove expansion revenue by identifying new use cases and stakeholders within existing accounts (~170%+ net revenue retention)
• Built and managed relationships with key customers including Drata, Synthesia, and Gorgias

• Generated enterprise pipeline through outbound into Fortune 500 accounts, including Kraft Heinz, Hershey, and PepsiCo
• Partnered with Account Directors on account planning and deal strategy, mapping stakeholders and creating qualified opportunities within target accounts
• Managed targeted outbound campaigns using cold calls, personalized email, and LinkedIn outreach
• Averaged 103% attainment against a $1.5M monthly pipeline generation quota
• Navigated large organizations to identify stakeholders and initiate sales cycles

• Onboarded new hires throughout their first 30 days, running mock calls and doing trainings.
• Built out enablement programs for Account Executives, including enablement around Outreach, Account mapping, Negotiation, and accessing power in deals.

• Promoted to Mid-Market level role after 7 months in the SMB role.

• Achieved 331% of quota in first month on full ramp.
• Achieved 125% to quota in Q2 and Q3.
• Used targeted questioning strategies to discover insight on prospect needs and requirements.
• Recorded and maintained sales prospect and sales data within Salesforce.
• Presented product concepts and offerings to clients based on established specifications and preferences.
• Managed sales cycle from first contact to established customer sale and maintained solid customer base.
• Trained and onboarded new sales reps and team members.
• Created enablement tools to improve efficiency of sales team.

• Successfully closed over $400,000 of ARR
• Secured 12-month and 6-month agreements
• Secured high-value accounts through consultative selling, effective customer solutions and promoting compelling business opportunities.
• Built and strengthened relationships with new and existing accounts to drive revenue growth.
• Presented key decision-makers with new and updated account strategies.

• Drove team revenue totals by bringing in over $10,000 in MRR.
• Collaborated with current and potential small businesses extensively to understand needs before proposing specific solutions.
• Established close relationships with new small business prospects.
• Contributed long-term sales strategy ideas to team to promote continuing business success.
• Developed and managed strong and growing pipelines of prospective small business customers.
• Researched potential clients and markets to prepare for appointments.
• Performed cold-calling and follow-ups with leads to secure new revenue.

• Managed 50 cold calls and 25 cold emails each day
• Identified prospect needs and developed appropriate responses along with information on suitable products and services
• Set up appointments with potential customers to discuss products and services
• Performed follow-ups with leads