SALES STRATEGY, AI & AUTOMATION

Grow Your Business Without Doing Everything Yourself.

You've set bigger goals. Now you need smarter ways to achieve them. Whether you need a stronger sales engine or AI and automation that actually work for your business, I'll help you turn your vision into measurable results.

Jenn Ritchie

The problem

You have a great product. Deals should be moving faster.

  • Interested prospects stall before they sign.
  • Buyers push back on price because the business case isn't clear.
  • Every seller runs a different process, and results depend on who is on the deal.
  • Your team spends hours on admin work that AI could handle, because your tools aren't designed to support how you actually sell.
  • You've built an amazing business and funnel and need to step out of selling to scale.

I've spent nearly two decades selling recruitment marketing and HR tech software. Now I use that experience to strengthen your sales.

Services

Three ways I help

01

AI Solutions & Automation

Put AI to work on the repetitive tasks holding your business back. I map your workflows, identify practical automation opportunities, and build and test custom AI solutions with your team.

Choose AI tools that fit your business, connect them to the way you work, and help your team adopt them with confidence.

Learn more →
02

Sales execution diagnosis and improvement

Find what's slowing your deals and fix it. I review live opportunities and sales practices, then improve discovery, value messaging, stakeholder alignment, and follow-up, working alongside your team on priority deals.

03

Go-to-market and sales process design

Build a path from interested prospect to signed customer that others can follow. For founders ready to move beyond founder-led sales: a clearly defined ideal customer profile (ICP) and target buyers, a sharper value story, defined sales stages, and a repeatable process.

Explore sales tech stack audits →

Prefer to send a message?

Tell me a little about your business and what you'd like help with. I'll get back to you personally.

Want to talk it through?

Send me your details and I'll get back to you personally.

HR Tech

Building an HR Tech Company? Let's Accelerate Your Growth.

You've built technology that can transform how companies hire, manage, and develop talent. Now you need the right sales strategy to get it into more hands.

I help HR Tech founders and revenue leaders turn ambitious growth goals into repeatable sales processes, stronger pipelines, and measurable results.

A track record built in complex, enterprise selling

113%
average quota attainment over 11 years at Greenhouse
4x
President's Club
#1 & #2
Global Seller at Greenhouse — 182% of quota in 2019 (#1) and 232% in 2022 (#2)
92%
team adoption of an AI platform, where I helped lead the proof of concept, saving up to 180 minutes per rep each week

Selected work

Connecting recruiting to revenue

Helped a growing services company tie hiring speed to revenue, building the business case that justified a premium solution.

Clearing a CFO blocker

Worked with technical partners to show a finance team exactly how a new system would connect to its financial planning, turning a stalled enterprise deal into a closed one.

AI workflows sellers actually use

Built six AI sales agents to streamline workflow, from RFP qualification to method-aligned follow-up, earning executive support for investment.

How I work

  1. 1

    Diagnose.

    We look at your deals, process, and tools together and agree on what matters most.

  2. 2

    Build.

    I roll up my sleeves on messaging, business cases, workflows, and priority deals, not just recommendations.

  3. 3

    Embed.

    Your team gets the coaching, templates, and habits to keep results going after I'm gone.

Discover What's Next in HR Technology

Heading to HR Tech 2026? I'm spotlighting innovative HR technology companies, sharing discoveries from the conference, and connecting great solutions with the people who need them.

Explore HR Tech Finds →
Jenn Ritchie

About

Hi, I'm Jenn.

I started in the TA/HR Tech space in Recruitment Advertising at Jobfox in 2007 and then sold at Yahoo HotJobs/Monster and Indeed. When I could not get my client's ATS systems to show the effectiveness and ROI on their ad spend, I decided to make the move to SaaS Sales and was fortunate to join JIBE (iCIMS acquired) team in 2013 and Greenhouse in 2015 as the 6th sales hire.

Working with Recruiting, TA, and People leaders has been such a career highlight for me. There is nothing better than helping someone find an amazing-fit job — one that betters their lives and future upside, and often the lives of their families too.

I've sold to mid-market and enterprise buyers, helped customers justify complex investments, built Greenhouse's first competitive-intelligence framework, trained and mentored new account executives, and helped introduce AI into everyday selling. Across 13 years in SaaS sales, I've guided thousands of software evaluations, so I know what a good one looks like from both sides of the table.

I'm also a certified professional coach, so I care as much about the people doing the selling as the process behind it. I bring a top seller's instincts, a coach's curiosity, and a practical approach to AI.

FAQ

Common questions

Who do you work with?

I work with two types of businesses: companies that want to grow through practical AI and automation, and HR Tech or B2B companies that need stronger sales execution and go-to-market strategies. Whether you're looking to streamline operations or accelerate revenue, I help turn ambitious goals into measurable results.

What can AI actually do for my business?

AI can help you capture opportunities, respond to customers, follow up with leads, and eliminate repetitive tasks that slow your business down. From AI voice and messaging agents to automated workflows, I help you identify where AI can make the biggest difference—and put practical solutions to work.

Do I need to understand AI to work with you?

Not at all. You don't need to know which tools to use or how to build an AI agent. That's where I come in. We'll start with what you want to accomplish, identify the right solutions, and make sure you understand how everything works.

You focus on running your business. I'll help make the technology work for you.

Can you build AI agents that answer calls, respond to messages, or follow up with leads?

Yes. I can help implement AI-powered voice, text, and email agents designed around your business needs. Whether you want to respond to inquiries faster, capture leads after hours, or improve follow-up, we'll build a solution that fits your processes and customer experience.

Will AI work with the systems and software I already use?

Often, yes. Many AI solutions can connect with existing CRMs, scheduling tools, email platforms, and other business software.

I'll evaluate your current systems first, identify what can be integrated, and recommend a practical approach. You shouldn't have to replace everything you've already invested in just to benefit from AI.

What happens after my AI solution is implemented?

Getting AI up and running is only the beginning. I can help with testing, refining workflows, training your team, and ongoing management so your solutions continue to support your business.

The goal isn't simply to launch an AI agent. It's to build something your business can actually rely on.

How much does AI implementation cost?

Every business has different needs, so pricing depends on the complexity of the solution, the systems involved, and the level of ongoing support required.

We'll start by identifying the opportunity and defining what success looks like. From there, I'll recommend a solution and provide a clear scope and pricing before any work begins.

Do you only advise, or do you do the work?

Both. I believe the best solutions combine strategy with execution. Whether we're improving your sales process or implementing AI agents and automations, I take a hands-on approach to building solutions that work. I also provide coaching and training so you and your team can use them confidently.

Can you help us choose sales software?

Yes. I help teams define what they actually need, run a focused evaluation, and pick sales tools and AI agents that fit their process and budget.

How do engagements work?

Each engagement is scoped to your goals after an initial conversation. We agree up front on deliverables, timing, and how we'll measure progress.

I have a different need. Could your skills still help?

Absolutely worth a conversation. Every business faces different challenges, and sometimes the biggest opportunities aren't immediately obvious. If you're looking to improve how your business operates, sells, or serves customers, let's explore what's possible.

What don't you do?

I don't design compensation plans, build territory models or restructure revenue organizations. I focus on how your team sells: deals, process, and the tools that support them.

Let's talk about what's holding your revenue growth back.

A 30-minute conversation to understand your goals and see whether I'm the right fit.