When Venkatesham started work on 1 June last year, he had high hopes.
"On my very first day, what I thought would be a realistic target for the men's first team would be competing for European places," he said.
Even though
Tottenham had just finished 17th under Ange Postecoglou, they had won the Europa League, their first trophy since 2008, while the squad was packed with seasoned internationals.
But reality quickly struck.
"If you'd have asked me a few months after I joined, when I was no longer an outsider, I would have told you the club was in a significantly worse state in some places than I thought," said Venkatesham.
"That is absolutely not meant to be a criticism of anyone or anything. It was just what I found. It was very clear that this wasn't some form of turnaround that was required of the club in quite a few areas. It was really a complete reset."
Asked to expand on that, Venkatesham said: "If I had to generalise, I would say on the non-football side of the club, in particular around stadium operations and commercial, that the club was and is really strong.
"I think if you look at the football side of the club, over a timeframe of five years or so, there has just been an explosion in progress across the Premier League.
"I'm not saying that
Tottenham didn't improve in that period. But what I can tell you is that when you look at where
Tottenham were in many of those areas, compared to where I believe other Premier League clubs are, there was a significant gap. In some areas really quite worryingly so.
"I don't think that there was what I would call a relentless obsession with football success.
"Our training centre is amazing, one of the best, if not the best in the world. But when you look around, it looks more like a five-star hotel than it does a performance environment. That will change over the summer.
"I think there are many areas where the club hasn't got the right level of expertise."
It means nothing now, but Frank's ill-fated reign started quite well following his appointment last June.
Tottenham lost just one of their opening 10 matches of the season in all competitions.
But when
Tottenham finally sacked Frank in February, the only surprise was that it didn't happen sooner.
Indeed, Venkatesham and sporting director Johan Lange faced heavy criticism from fans for prolonging Frank's tenure for as long as they did.
"There's been plenty of coverage that the club was passive during this period. And that's absolutely not true," insisted Venkatesham.
In weighing up Frank's future, Venkatesham says the club considered results, the probability of the Dane turning their failing season around, concerns changing managers may create in the January transfer window, the fixture calendar and concerns over entering the interim head coach market.
Venkatesham confirmed to BBC Sport that
Tottenham tried to entice De Zerbi, who was leaving Marseille, to become the club's full-time head coach after Frank was dismissed.
The Italian, however, was originally unwilling to take the job mid-season, which led Spurs towards making the left-field appointment of Tudor – who left Spurs by mutual consent after just seven games.
"Obviously, we were very disappointed when it became clear that we wouldn't be appointing Roberto on a permanent basis [in February]," said Venkatesham.
"We were then, in the interim market, which is generally not the broadest. There were a number of reasons why Igor was selected: he had managed in very high-profile and high-pressure environments - we didn't want somebody that was going to wilt under that pressure.
"He has a history of making an immediate impact. He has managed in big clubs. He has quite a different personality to Thomas and we felt like something different was needed.
"But of course we were really aware he had no Premier League experience. Was it a risk in appointing him? Absolutely."
Asked if he would accept the Tudor appointment was a mistake, Venkatesham responded: "It didn't work out. I think it's very clear it didn't work out. And I don't think that is in question. I don't think anybody would argue anything else."
Former executive chairman Daniel Levy,
who left Tottenham in September after 25 years, was generally the target of supporters ire during his long reign.
But since Levy's exit, Venkatesham has attracted increasing anger from irate sections of the fanbase.
Asked if the abuse from supporters has forced him to consider his own role at the club, Venkatesham said: "I understand the frustration around supporters. I think
Tottenham supporters have been frustrated for some time. This is two 17th-place finishes in a row.
"It's clearly not good enough. I think that is rational, normal, sensible, and, is what we would expect from supporters.
"The club had some serious challenges that it needs to address on the football side. We know what those are. We are addressing them. We are fixing them. Those challenges have not disappeared overnight.
"They built up over many years. I wish I could wave my magic wand and fix them overnight, but that is not possible. It takes some time to fix those issues.
"So I have complete confidence in what we're doing, how we're doing it. But supporters are rightly impatient. So I have to weather that storm."
On dealing with intense criticism from fans, Venkatesham - who previously worked for Woolwich - added: "It's not easy. You have to develop a thick skin.
"I'm helped by the fact that I've been in football for a while, for the last 15 years, so it's not new to me.
"It's a game of opinions, and I have absolutely no problem with being criticised. I've got no problem what anyone in the game being criticised, it's just part of the job.
"The challenge in football is that that criticism frequently goes way past the line for players, referees, executives."
Speak to those behind the scenes at
Tottenham, they will tell you that De Zerbi's impact has been profound.
Not only in picking up 11 points from seven games to preserve the club's top-flight status, but his growing influence is instilling belief in the squad.
"I think he has made an extraordinary impact so far," Venkatesham said.
"We have to recognize that it's early days, and we also need to recognize that he's come into a very specific situation.
"It is hard to underestimate the scale of the challenge he walked into. And it's hard to describe what a significant impact he has had in the dressing room with all the players.
"I think he's an excellent coach, and we think that he plays the style of football that our supporters and the broader football public want to see."
De Zerbi is expected to have full involvement in the club's recruitment this summer.
Tottenham have held talks with Borussia Dortmund's departed sporting director Sebastian Kehl, while Venkatesham confirmed the club have raised their wage ceiling in the hope of attracting top-quality players.
"The squad needs work and the squad hasn't got the right balance," he said.
"We need experience and leadership and also that kind of physical robustness to play in the most demanding league that exists.
"We need to strengthen the club over multiple transfer windows but this transfer window, in particular, is going to be critical."
CJJ was joking.
