Skip to content
BackNov 7
Jennifer H.
Upwork badge

Jennifer H.

Expert Full Cycle Sales | AI Powered Workflows I Lead Gen and GTM

I bring 20+ years of hands-on B2B sales and business development experience, helping startups, growth-stage companies, and enterprise organizations drive revenue through outbound sales, lead generation, cold calling, affiliate partnerships, pipeline development, and full-cycle closing. I specialize in enterprise sales, strategic account development, revenue growth, customer acquisition, and complex B2B sales cycles. My experience includes working directly with C-suite executives and senior decision-makers, navigating government and education procurement processes, managing high-value accounts, and closing multimillion-dollar contracts. I build predictable sales pipelines, develop long-term client relationships, and turn qualified prospects into revenue. Accomplishments: -$5M in new revenue for a software company by closing large government and education accounts -40% increase in customer base and revenue in 60 days for a startup -30% sales increase for a SaaS client through a partnership program I developed -$3M in total revenue in my best year across multiple industries -$2.5M in new policy premium in year one as a top-producing insurance agent, earning multiple awards for highest new account acquisition -Built and led a team of 7+ sales reps to regional award winning status , while exceeding my own sales targets What I Do I own the entire sales cycle: prospecting, lead generation, pipeline management, discovery calls, presentations, negotiation, and closing. I self-source leads through cold calling, LinkedIn, email campaigns, and strategic partnerships. I've closed high-ticket B2B deals in SaaS, software development, government contracts, IT services, healthcare, insurance, and real estate. I know how to navigate long sales cycles and complex procurement processes. How I Work I built my sales career from scratch — cold-calling daily, self-sourcing 100% of leads, and closing deals across medical practices, manufacturing, professional services, and enterprise accounts. I'm HubSpot Advanced Certified and proficient in Salesforce, Pipedrive, LinkedIn, Sales Navigator, Apollo, and Outreach. I use data and CRM analytics to optimize performance, but I close deals through real conversations and relationships. AI Sales Systems & AI Workflows | I build AI-powered sales processes and workflows to eliminate repetitive tasks, reduce costs, and accelerate lead generation. I use Claude, ChatGPT, Cowork, Hubspot and Apollo for prospect research, targeted list building, personalized outreach, and CRM workflows. AI helps me scale efficiently, but real conversations on the phone and relationships are what close deals. I use AI to reach the right decision-makers faster so I can spend more time selling. Who I Work With Startups building their first sales engine, growth-stage companies scaling revenue, and enterprises launching new products. I take full accountability for bringing on new accounts and generating revenue. You're hiring 20+ years of proven expertise and someone who delivers results from day one. My rate is $95/hr with a minimum 2-week engagement to start. I'm open to discussing hybrid compensation structures after an initial engagement period once we've established a working relationship and there's a clear path to earnings. Commission-only arrangements are not a fit

🇺🇸Detroit, United States$95/hr100% JSS4.92 (79)Since Nov 2015

Earnings and projects

MRR
$11k

Last 6 months ÷ 6

World#972 / 412k
🇺🇸Country#468 / 62.1k
Revenue, last 30 days
$9.5k

Last 6 months: $67k

World#1,618 / 412k
🇺🇸Country#718 / 62.1k
Total earnings
$544k

Billed in all: $565k

World#2,294 / 412k
🇺🇸Country#810 / 62.1k
Per project
$4.9k

$3.5k in the last 6 months

World#35,466 / 412k
🇺🇸Country#5,877 / 62.1k
Projects, last 6 months
19
42% fixed58% hourly
World#6,608 / 412k
🇺🇸Country#1,138 / 62.1k
Projects in all
111

Across 146 contracts

18% fixed82% hourly
World#24,175 / 412k
🇺🇸Country#3,901 / 62.1k

Earnings, last 30 days

$565k+$9.5k earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$555k$560k$565k$570kOct 8Oct 23Nov 7

Skill rankings: #1 in 1 skill of 15

Rarest: top 0.06% in Cold Calling, of 6,565. Ranked by MRR among everyone on Upwork with the skill.

  1. 1High-Ticket Closing404 freelancers · 🇺🇸 #1Top 0.25%
  2. 2Appointment Scheduling3,126 freelancers · 🇺🇸 #1Top 0.06%
  3. 2Affiliate Marketing1,317 freelancers · 🇺🇸 #2Top 0.15%
  4. 3Customer Acquisition639 freelancers · 🇺🇸 #3Top 0.47%
  5. #4Cold Calling6,565 freelancers · 🇺🇸 #4Top 0.06%
  6. #5B2B Lead Generation4,880 freelancers · 🇺🇸 #3Top 0.10%
  7. #6Outbound Sales4,644 freelancers · 🇺🇸 #6Top 0.13%
  8. #7Outreach Strategy1,628 freelancers · 🇺🇸 #5Top 0.43%