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During Season Three of Silicon Valley, Pied Piper founder Richard is fired and replaced as Chief Executive Officer (CEO) by “Action” Jack Barker. The belief is that Richard isn’t ready for prime time and Barker, an old school, and long time leader in the tech field, is what the start-up needs to get to the next level. That the team at Pied Piper isn’t happy about this change is to be expected, that things don’t go quite as planned, is not, and what this story line deftly points out, is how unnerving it can be when your start-up is ready to hire an executive or add to the executive team. If your company is going to evolve, and you’re going to take your business to the next level of growth and beyond, you eventually need to build out your leadership team. But to be successful, a dedicated plan, and understanding of your strengths, weakness and needs, is essential. You can begin crafting your plan by asking yourself the following questions, all of which are common among founders:
Know your organization’s strengths and understand where there are gaps. Also, make sure your leadership hires fill those gaps and complement your existing team. For example, the CEO has to be a strategic thinker, understanding where the field is heading and betting they know what your consumers will want before they do. This was one of Steve Jobs’ greatest gifts, he didn’t react to what consumers said they wanted, he showed them before they even knew to ask for it. CEOs also have to be able to rise above the day to day minutiae and struggles of running a company, something that Richard cannot allow himself to do at Pied Piper, but something Jack is quite capable of achieving. For additional thoughts on the role of the CEO, as well as positions such as Chief Operating Officer, Chief Marketing Officer, and so on, Entrepreneur Magazine, does a nice job of illustrating their respective responsibilities.
In Silicon Valley, “Action” Jack is brought in, because Richard and the Pied Piper team have gone as far as they can go on their own. They need someone with vision and a steady hand. They also need a cheerleader and a leader who can bring them together as a team. Up until now it’s their underdog status and ongoing problems that have allowed them to focus and bond together. The right time to add a new executive is when you’re ready to grow, the opportunity to grow is present and that growth will only be restrained by poor leadership and the inability to work as a team. Any challenge that serves to leave you stuck in where you’ve been and not where you want to go, be that vision, financial or branding, is a potential role to be filled, and when you company is stuck, that’s the right time to bring in new people, new ideas and new executives.
It can be an unnerving time when your start-up is ready to hire an executive or add to the executive team in an effort to take the business to the next growth level and beyond.
But that’s why you need a plan.
First though, ask yourself whether it is the right time and then, what you’re seeking in this position.
Look at your strengths and weaknesses and ask yourself what the right person would look like.
After that, do market research, determine what you can realistically pay and whether the right person would be interested in this job.
Then engage in your search, and if you cannot find the right candidate, refine it.
Hirewell is Your Partner to Help You Find the Right Executive for Your Organization. We’re here to provide you with the knowledge and support you need to get your plan started.
Over the last year, hiring teams have started seeing a wave of new job titles pop up across tech, sales, and operations.
Some are legitimate new roles.
Others are existing jobs with a slightly different name.
And many of them have one thing in common: AI is suddenly part of the job description.
From Go-to-Market Engineers to AI Specialists, companies are experimenting with new roles as they figure out how automation and AI fit into their teams.
But most of these positions aren’t entirely new. They’re evolutions of existing roles.
One role that is gaining traction is the Go-to-Market Engineer.
Depending on who you ask, it is either:
In practice, it is a bit of both.
As Matt Tokarz recently pointed out after closing a search for an Outbound & Go-to-Market Specialist, the role looked very different from traditional RevOps. The focus was not reporting or CRM hygiene. It was building prompts, leveraging tools like Clay and Smartlead, and enabling SDRs and AEs with backend insights to accelerate pipeline growth.
Instead of traditional RevOps work like reporting and CRM management, the focus was on:
The goal was not simply managing sales data. It was accelerating pipeline generation through automation.
One trend is becoming clear. Companies are not replacing entire departments with AI.
Instead, they are changing how existing roles operate.
Sales teams still need pipeline.
Marketing teams still need content.
Engineering teams still need to build software.
The difference is that employers now expect candidates to use AI tools as part of their workflow.
As Zac Colip noted during the discussion, we are currently in a transitional phase where companies are labeling roles with “AI” as they experiment with how the technology fits into teams.
But that may not last forever.
Right now, AI still feels new enough that companies highlight it in job titles.
But eventually, AI will likely become a baseline expectation, not a specialty.
Think about it like cloud technology or data analytics.
At first, companies hired “cloud specialists.” Now most engineers are expected to understand cloud infrastructure.
The same shift will likely happen with AI.
Instead of hiring “AI-enabled marketers” or “AI engineers,” companies will simply expect employees to know how to work with AI tools.
One challenge with these emerging roles is simple: there aren’t many candidates with real experience yet.
Many of these positions didn’t exist two years ago.
In one recent search, we started looking for a candidate locally in Chicago. Eventually we expanded nationwide because the pool of people with relevant experience was extremely limited.
This is a common issue with emerging roles:
That gap will likely persist for the next few years.
Another noticeable shift is that roles are becoming more hybrid.
Instead of hiring for narrow responsibilities, companies are combining multiple functions into one position.
As Matt Mulcahy highlighted, one example is the rise of Forward Deployed Engineers, a model popularized by Palantir.
These engineers:
What used to involve several roles, including product managers, engineers, and solution architects, can now sometimes be handled by one person. AI development tools are part of what makes this possible.
Not every industry is moving at the same pace.
As Ashley DuBois pointed out, some sectors, such as transportation, are applying AI to specific workflows like load booking and operational automation.
At the same time, some companies are adding “AI” to job titles even when the core responsibilities remain largely traditional.
In many cases, it is still essentially an IT manager role with AI familiarity layered in.
This reflects a broader transition period where companies want to signal modernization and candidates want to signal relevance.
In logistics, AI is increasingly handling scheduling, tracking, and coordination tasks.
According to Brittany Lasky, operational roles such as logistics coordinators may experience the greatest impact from automation.
However, freight brokers who manage negotiation and strategic RFPs remain in demand.
AI can optimize processes. It does not replace relationship management or strategic negotiation.
Across industries, a pattern is emerging.
Execution becomes automated. Strategy becomes more valuable.
Automation is also reshaping finance and accounting roles.
As Adam Slater noted, accounts receivable jobs that once focused on high-volume manual processing are evolving into more analytical positions centered on reporting and insights.
The work is not disappearing. The expectations are increasing.
Organizations are now hiring for:
Even roles traditionally considered administrative now require deeper technical capability.
AI is not eliminating analyst roles. It is expanding them.
Financial analysts are also expected to understand tooling, sourcing, and data transformation.
In many cases, two or three roles are being combined into one.
This raises a long-term question.
If entry-level roles become more complex or disappear entirely, how will organizations develop senior talent in the future?
The traditional model of high-volume cold calling is changing.
According to Jack Smith and Emily Canna, teams are shifting toward:
At the same time, companies are moving away from activity-based KPIs and focusing more on outcomes such as demos set and SQLs generated.
In a market saturated with automated outreach, authentic communication has become a competitive advantage.
Several clients have said it directly. They want a human in the seat.
Every six to twelve months, hiring trends in go-to-market teams shift.
As Jennifer Salerno noted, companies move through cycles.
One quarter it is BDRs.
Then RevOps.
Now it is go-to-market engineers.
Many companies experimented heavily with AI to accelerate pipeline generation.
What those experiments exposed were structural gaps, particularly in outbound strategy.
AI can support execution. It does not replace a well-built top-of-funnel engine.
Inbound momentum can hide weaknesses. Outbound forces clarity.
The companies gaining traction right now are not chasing trends. They are rebuilding the fundamentals of their go-to-market strategy.
For employers, the takeaway is straightforward. Job descriptions and expectations need to evolve alongside technology.
Across functions, we are seeing the same shift play out. AI is not eliminating entire roles. It is changing how those roles operate and increasing the baseline skill set required to perform them well.
Hiring managers should start thinking less about traditional titles and more about capabilities. That often means prioritizing candidates who can:
In many cases, the perfect candidate with the exact title simply does not exist yet. The strongest hires are often people who have developed adjacent skills and shown the ability to adapt as the tools evolve.
The broader trend is that AI is accelerating a shift that was already underway.
Roles are becoming more hybrid. Expectations are increasing across nearly every function. And repetitive tasks are being automated, leaving more strategic work behind.
Sales teams still need pipeline.
Operations teams still need coordination.
Finance teams still need reporting and analysis.
Engineering teams still need to build software.
What is changing is how the work gets done and what skills are required to do it well.
Right now we are in a transitional phase where companies are still labeling roles with “AI” as they experiment with new workflows and technologies.
Over time, that label may disappear.
AI will simply become part of how work gets done.
And the roles themselves, while evolving, will look more familiar than the titles might suggest.