Meet Our New Chief People Officer

Jessi Howard will lead Rally’s HR practice and operate as a fractional CPO for the Rally portfolio.

4 min readSep 14, 2021


We’re excited to announce that Jessi Howard is joining Rally Ventures as our Chief People Officer (CPO). She will lead Rally’s HR practice and operate as a fractional CPO for the Rally portfolio, providing strategic guidance and tactical support.

Jessi brings 20+ years of experience in tech HR to the firm, having helped grow and shape multiple tech start-ups, including SportsEngine, RedBrick Health and Secure Computing.

Jessi’s newly-designed role as Fractional CPO will provide Rally Ventures’ portfolio of emerging companies with access to an executive level head of talent in order to drive results and accelerate milestones. She’ll focus on designing foundational HR practices for the portfolio, attracting best-in-class talent and supporting the exceptional people building industry-altering companies.

Human resources and recruitment are critical components in the success of early-stage companies, but most startups don’t have the need or resources for a full-time position until they reach a later stage. Her addition to the Rally team underscores our belief that people are at the absolute core of success in SaaS.

Jessi is a world-class HR executive with deep experience in early-stage technology, and we’re thrilled to have her join our team. Welcome, Jessi!

The job market right now is HOT! High-quality talent is in demand and most early-stage companies have few HR resources to lean on during the recruitment process. Here are a few of Jessi’s top tips on how you can stand out and attract top talent.

Write an Effective Job Posting

Take the time to write an effective job posting. Job seekers don’t know who you are yet. Include a sentence or two that explains what you do and make it compelling! Give job seekers a reason to read on.

It’s also important to use the right job title and keywords. Try to think like a job seeker. How would they look for a job and what would they want to know? Typically, job seekers search for jobs by title, keyword and location.

Avoid using titles you might use internally or you think are hip. Advertising for a Software Rockstar probably won’t yield much. But a posting for a Software Engineer — Full Stack, using keywords such as the tech stack you work with, will help attract a better match.

Optimize Job Distribution

So now you’ve written a fantastic job description. How are job seekers going to see it? This can be one of the biggest challenges for start-ups that don’t have an HR system or applicant tracking system in place.

Attracting new talent to grow your business will be a constant need. At some point, you’ll want to invest in an applicant tracking system (ATS), which has multiple benefits. Most applicant tracking systems offer automated distribution to job board aggregators through a nightly scrape of your site, which can vastly enhance the web presence of your job postings. An ATS also makes for a better applicant experience, with tools to send auto replies and keep candidates updated.

Whether an ATS is in the budget or not, posting jobs on LinkedIn is also a good option. You can post jobs for free from your company page. Learn how here. Job seekers will need to navigate to your Company page to find your jobs, so you’ll want to be sure to harness the power of the people in your organization to share the job posting links with their networks.

Lastly, take advantage of other free postings available and work on building partnerships. If you are interested in hiring new grads, Handshake is a nationwide college job posting site you’ll want to check out. Do you like boot camp grads? Build a relationship with the Career Placement Advisor in your town. They are always looking for involvement from the local tech community.

Stand Out During the Interview

The competition for talent is fierce right now! If you are lucky enough to get an applicant interested in speaking with you, don’t mess it up with a sloppy interview process or lack of follow up.

Plan who is going to cover what in the interview and be sure someone is taking the role of salesperson with authentic, transparent information about why someone should join the company. The best way to do this is to really listen during the interview process. What does the candidate need to feel fulfilled? If it’s something you can offer, tell them that. Customize your conversation to speak the language that will resonate with them, not just your usual pitch. You’ll be surprised.

And whatever you do, please make sure you do not neglect closing the loop with those you don’t hire. Every interaction matters in building your reputation. What a perfect time to get it right. Go be great!



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