Personal blog of Yzmir Ramirez

Many enterprise software startups at some point have faced the invisible wall. For months, your sales team has done everything right. They’ve met with a prospect several times, provided them with demos, free trials, documentation and references, and perhaps even signed a provisional contract.

The stars are all aligned and then, suddenly, the deal falls apart. Someone has put the kibosh on the entire project. Who is this deal-blocker and what can software companies do to identify, support and convince this person to move forward with a contract?

I call this person the Chief Objection Officer.

Most software companies spend a lot of time and effort identifying their potential buyers and champions within an organization. They build personas and do targeted marketing to these individuals and then fine-tune their products to meet their needs. These targets may be VPs of engineering, data leaders, CTOs, CISOs, CMOs or anyone else with decision-making authority. But what most software companies neglect to do during this exploratory phase is to identify the person who may block the entire deal.

This person is the anti-champion with the power to scuttle a potential partnership. Like your potential deal-makers, these deal-breakers can have any title with decision-making power. Chief Objection Officers aren’t simply potential buyers who end up deciding your product is not the right fit, but are instead blockers-in-chief who can make departmentwide or companywide decisions. Thus, it’s critical for software companies to identify the Chief Objection Officers that might block deals and, then, address their concerns.

So how do you identify the Chief Objection Officer? The trick is to figure out the main pain points that arise for companies when considering deploying your solution, and then walk backward to figure out which person these challenges impact the most. Here are some common pain points that your potential customers may face when considering your product.

Change is hard. Never underestimate the power of the status quo. Does implementing your product in one part of an organization, such as IT, force another department, such as HR, to change how they do their daily jobs?

Think about which leaders will be most reluctant to make changes; these Chief Objection Officers will likely not be your buyers, but instead the heads of departments most impacted by the implementation of your software. For example, a marketing team may love the ad targeting platform they use and thus a CMO will balk at new database software that would limit or change the way customer segment data is collected. Or field sales would object to new security infrastructure software that makes it harder for them to access the company network from their phones. The head of the department that will bear the brunt of change will often be a Chief Objection Officer.

Is someone’s job on the line?

Another common pain point when deploying a new software solution is that one or more jobs may become obsolete once it’s up and running. Perhaps your software streamlines and outsources most of a company’s accounts payable processes. Maybe your SaaS solution will replace an on-premise homegrown one that a team of developers has built and nurtured for years.

It wasn’t so long ago that sales meant just showing up with a deck and a smile. These days, it seems that sales leaders almost need a PhD in statistics just to get through the typical day managing a sales funnel. From SQLs and MQLs to NDRR and managing overall retention, the roles of VP of Sales and Chief Revenue Officers (CROs) are evolving rapidly in tandem with the best practices of SaaS startups.

Few people know this world better than David Ives, who is a partner at True Search, one of the top executive recruiting firms in the country where he co-leads the go-to-market practice. David has led countless CRO and VP of Sales searches, and in the process, has learned not just what CEOs and boards are looking for, but also the kinds of skills that candidates need to shine in these important career inflection points.

In our conversation, we talk about the evolving nature of the sales org, how leaders can best position themselves for future advancement, what companies are looking for today in new executive sales hires, and compensation changes in the industry.

This interview has been extensively edited and condensed for clarity

Introduction and background

Danny: Why don’t we start with your background — how did you get into recruiting?

David: So my background was definitely unique. I started as an enterprise sales rep of the truest form selling subscription-based data analytics and systems into capital markets, so into investment banks, trading desks, hedge funds, asset managers, portfolio managers — you name it. Then I drifted purposely, intentionally away from capital markets and did about four different growth technology companies. I landed at NewsCred, and it was a neat time — it was really the birth of the startup landscape with the whole Flatiron district in New York.

Later, I was looking for my next CRO opportunity and was networking with some of the investor folks that I knew. I had a friend of mine who was a talent partner at a private equity firm who said to me, “I’ve always thought that you’d be really good at this and we’re starting to push for our search firms to have operators.” I went and met with Brad and Joe [founders of True], and three weeks later I was in the seat.

Danny: That’s great. And what do you do at True?

David: Well, we moved to a specialization model right when I got here. I don’t know if I was the test case or not, but I didn’t know search, so my skillset was that I knew the role. I run our go-to-market practice with another partner, and we have probably 40, 45 people in that group. We focus exclusively on sales, marketing, customer success, we’ll do biz dev. I probably skew more to CRO than anything else, but I do CMO and VP of marketing as well, and then I do a handful of business development, chief client officers, and VPs of customer success a year. That’s my mix basically.

What is the skillset of a modern CRO?

Danny: You’ve been in the sales leadership space for a long time, and you’ve been in the recruiting space for a couple of years. What are some of the changes that you’re seeing today in terms of candidates, skills, and experiences?

David: I think a big change has been from what I call a backend pipeline manager to what I would call a full funnel manager.

 For early- to mid-stage B2B software and SaaS companies, selling in to the enterprise is hard. Getting enterprise customers to pay for your solution on a repeated and long-term basis without seeing your sales growth stall out? That’s really hard. Welcome to the challenging world of enterprise sales. Many factors are in play, including competitive challenges, timing issues and product… Read More